Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids

The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of sil...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Qin Pan [verfasserIn] Yong Wu [verfasserIn] Aqun Zheng [verfasserIn] Xiangdong Wang [verfasserIn] Xiaoyong Li [verfasserIn] Wanqin Wang [verfasserIn] Min Gao [verfasserIn] Zainab Bibi [verfasserIn] Sidra Chaudhary [verfasserIn] Yang Sun [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2023

Schlagwörter:	ball milling Suzuki–Miyaura cross-coupling 1 PdO silica gel

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 28(2023), 7190, p 7190
Übergeordnetes Werk:	volume:28 ; year:2023 ; number:7190, p 7190

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules28207190

Katalog-ID:	DOAJ093098308

Internformat


LEADER	01000naa a22002652 4500
001	DOAJ093098308
003	DE-627
005	20240413215416.0
007	cr uuu---uuuuu
008	240413s2023 xx \|\|\|\|\|o 00\| \|\|eng c
024	7		\|a 10.3390/molecules28207190 \|2 doi
035			\|a (DE-627)DOAJ093098308
035			\|a (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b
040			\|a DE-627 \|b ger \|c DE-627 \|e rakwb
041			\|a eng
050		0	\|a QD241-441
100	0		\|a Qin Pan \|e verfasserin \|4 aut
245	1	0	\|a Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids
264		1	\|c 2023
336			\|a Text \|b txt \|2 rdacontent
337			\|a Computermedien \|b c \|2 rdamedia
338			\|a Online-Ressource \|b cr \|2 rdacarrier
520			\|a The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals.
650		4	\|a ball milling
650		4	\|a Suzuki–Miyaura cross-coupling
650		4	\|a 1<i<H</i<-indazole
650		4	\|a PdO<sub<2</sub< nanoparticle
650		4	\|a silica gel
653		0	\|a Organic chemistry
700	0		\|a Yong Wu \|e verfasserin \|4 aut
700	0		\|a Aqun Zheng \|e verfasserin \|4 aut
700	0		\|a Xiangdong Wang \|e verfasserin \|4 aut
700	0		\|a Xiaoyong Li \|e verfasserin \|4 aut
700	0		\|a Wanqin Wang \|e verfasserin \|4 aut
700	0		\|a Min Gao \|e verfasserin \|4 aut
700	0		\|a Zainab Bibi \|e verfasserin \|4 aut
700	0		\|a Sidra Chaudhary \|e verfasserin \|4 aut
700	0		\|a Yang Sun \|e verfasserin \|4 aut
773	0	8	\|i In \|t Molecules \|d MDPI AG, 2003 \|g 28(2023), 7190, p 7190 \|w (DE-627)311313132 \|w (DE-600)2008644-1 \|x 14203049 \|7 nnns
773	1	8	\|g volume:28 \|g year:2023 \|g number:7190, p 7190
856	4	0	\|u https://doi.org/10.3390/molecules28207190 \|z kostenfrei
856	4	0	\|u https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b \|z kostenfrei
856	4	0	\|u https://www.mdpi.com/1420-3049/28/20/7190 \|z kostenfrei
856	4	2	\|u https://doaj.org/toc/1420-3049 \|y Journal toc \|z kostenfrei
912			\|a GBV_USEFLAG_A
912			\|a SYSFLAG_A
912			\|a GBV_DOAJ
912			\|a GBV_ILN_20
912			\|a GBV_ILN_22
912			\|a GBV_ILN_23
912			\|a GBV_ILN_24
912			\|a GBV_ILN_39
912			\|a GBV_ILN_40
912			\|a GBV_ILN_60
912			\|a GBV_ILN_62
912			\|a GBV_ILN_63
912			\|a GBV_ILN_65
912			\|a GBV_ILN_69
912			\|a GBV_ILN_70
912			\|a GBV_ILN_73
912			\|a GBV_ILN_95
912			\|a GBV_ILN_105
912			\|a GBV_ILN_110
912			\|a GBV_ILN_151
912			\|a GBV_ILN_161
912			\|a GBV_ILN_170
912			\|a GBV_ILN_206
912			\|a GBV_ILN_213
912			\|a GBV_ILN_224
912			\|a GBV_ILN_230
912			\|a GBV_ILN_285
912			\|a GBV_ILN_293
912			\|a GBV_ILN_602
912			\|a GBV_ILN_2005
912			\|a GBV_ILN_2009
912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2055
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_4012
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4249
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4306
912			\|a GBV_ILN_4307
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4322
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4325
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4367
912			\|a GBV_ILN_4700
951			\|a AR
952			\|d 28 \|j 2023 \|e 7190, p 7190

Indexfelder

author_variant	q p qp y w yw a z az x w xw x l xl w w ww m g mg z b zb s c sc y s ys
matchkey_str	article:14203049:2023----::ehnceiasnhssfdsbsbaoatceimblzdvriiaefraayiszkmyuarsculnratosedntte3
hierarchy_sort_str	2023
callnumber-subject-code	QD
publishDate	2023
allfields	10.3390/molecules28207190 doi (DE-627)DOAJ093098308 (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b DE-627 ger DE-627 rakwb eng QD241-441 Qin Pan verfasserin aut Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals. ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel Organic chemistry Yong Wu verfasserin aut Aqun Zheng verfasserin aut Xiangdong Wang verfasserin aut Xiaoyong Li verfasserin aut Wanqin Wang verfasserin aut Min Gao verfasserin aut Zainab Bibi verfasserin aut Sidra Chaudhary verfasserin aut Yang Sun verfasserin aut In Molecules MDPI AG, 2003 28(2023), 7190, p 7190 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:7190, p 7190 https://doi.org/10.3390/molecules28207190 kostenfrei https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b kostenfrei https://www.mdpi.com/1420-3049/28/20/7190 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 7190, p 7190
spelling	10.3390/molecules28207190 doi (DE-627)DOAJ093098308 (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b DE-627 ger DE-627 rakwb eng QD241-441 Qin Pan verfasserin aut Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals. ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel Organic chemistry Yong Wu verfasserin aut Aqun Zheng verfasserin aut Xiangdong Wang verfasserin aut Xiaoyong Li verfasserin aut Wanqin Wang verfasserin aut Min Gao verfasserin aut Zainab Bibi verfasserin aut Sidra Chaudhary verfasserin aut Yang Sun verfasserin aut In Molecules MDPI AG, 2003 28(2023), 7190, p 7190 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:7190, p 7190 https://doi.org/10.3390/molecules28207190 kostenfrei https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b kostenfrei https://www.mdpi.com/1420-3049/28/20/7190 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 7190, p 7190
allfields_unstemmed	10.3390/molecules28207190 doi (DE-627)DOAJ093098308 (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b DE-627 ger DE-627 rakwb eng QD241-441 Qin Pan verfasserin aut Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals. ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel Organic chemistry Yong Wu verfasserin aut Aqun Zheng verfasserin aut Xiangdong Wang verfasserin aut Xiaoyong Li verfasserin aut Wanqin Wang verfasserin aut Min Gao verfasserin aut Zainab Bibi verfasserin aut Sidra Chaudhary verfasserin aut Yang Sun verfasserin aut In Molecules MDPI AG, 2003 28(2023), 7190, p 7190 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:7190, p 7190 https://doi.org/10.3390/molecules28207190 kostenfrei https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b kostenfrei https://www.mdpi.com/1420-3049/28/20/7190 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 7190, p 7190
allfieldsGer	10.3390/molecules28207190 doi (DE-627)DOAJ093098308 (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b DE-627 ger DE-627 rakwb eng QD241-441 Qin Pan verfasserin aut Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals. ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel Organic chemistry Yong Wu verfasserin aut Aqun Zheng verfasserin aut Xiangdong Wang verfasserin aut Xiaoyong Li verfasserin aut Wanqin Wang verfasserin aut Min Gao verfasserin aut Zainab Bibi verfasserin aut Sidra Chaudhary verfasserin aut Yang Sun verfasserin aut In Molecules MDPI AG, 2003 28(2023), 7190, p 7190 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:7190, p 7190 https://doi.org/10.3390/molecules28207190 kostenfrei https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b kostenfrei https://www.mdpi.com/1420-3049/28/20/7190 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 7190, p 7190
allfieldsSound	10.3390/molecules28207190 doi (DE-627)DOAJ093098308 (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b DE-627 ger DE-627 rakwb eng QD241-441 Qin Pan verfasserin aut Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals. ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel Organic chemistry Yong Wu verfasserin aut Aqun Zheng verfasserin aut Xiangdong Wang verfasserin aut Xiaoyong Li verfasserin aut Wanqin Wang verfasserin aut Min Gao verfasserin aut Zainab Bibi verfasserin aut Sidra Chaudhary verfasserin aut Yang Sun verfasserin aut In Molecules MDPI AG, 2003 28(2023), 7190, p 7190 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:7190, p 7190 https://doi.org/10.3390/molecules28207190 kostenfrei https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b kostenfrei https://www.mdpi.com/1420-3049/28/20/7190 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 7190, p 7190
language	English
source	In Molecules 28(2023), 7190, p 7190 volume:28 year:2023 number:7190, p 7190
sourceStr	In Molecules 28(2023), 7190, p 7190 volume:28 year:2023 number:7190, p 7190
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel Organic chemistry
isfreeaccess_bool	true
container_title	Molecules
authorswithroles_txt_mv	Qin Pan @@aut@@ Yong Wu @@aut@@ Aqun Zheng @@aut@@ Xiangdong Wang @@aut@@ Xiaoyong Li @@aut@@ Wanqin Wang @@aut@@ Min Gao @@aut@@ Zainab Bibi @@aut@@ Sidra Chaudhary @@aut@@ Yang Sun @@aut@@
publishDateDaySort_date	2023-01-01T00:00:00Z
hierarchy_top_id	311313132
id	DOAJ093098308
language_de	englisch
fullrecord	<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000naa a22002652 4500</leader><controlfield tag="001">DOAJ093098308</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20240413215416.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">240413s2023 xx \|\|\|\|\|o 00\| \|\|eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.3390/molecules28207190</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)DOAJ093098308</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="050" ind1=" " ind2="0"><subfield code="a">QD241-441</subfield></datafield><datafield tag="100" ind1="0" ind2=" "><subfield code="a">Qin Pan</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2023</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">ball milling</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Suzuki–Miyaura cross-coupling</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">1<i<H</i<-indazole</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">PdO<sub<2</sub< nanoparticle</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">silica gel</subfield></datafield><datafield tag="653" ind1=" " ind2="0"><subfield code="a">Organic chemistry</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Yong Wu</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Aqun Zheng</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Xiangdong Wang</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Xiaoyong Li</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Wanqin Wang</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Min Gao</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Zainab Bibi</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Sidra Chaudhary</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Yang Sun</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">In</subfield><subfield code="t">Molecules</subfield><subfield code="d">MDPI AG, 2003</subfield><subfield code="g">28(2023), 7190, p 7190</subfield><subfield code="w">(DE-627)311313132</subfield><subfield code="w">(DE-600)2008644-1</subfield><subfield code="x">14203049</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:28</subfield><subfield code="g">year:2023</subfield><subfield code="g">number:7190, p 7190</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doi.org/10.3390/molecules28207190</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://www.mdpi.com/1420-3049/28/20/7190</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="u">https://doaj.org/toc/1420-3049</subfield><subfield code="y">Journal toc</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_DOAJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_20</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_22</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_23</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_39</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_40</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_60</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_63</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_65</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_73</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_95</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_105</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_151</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_161</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_170</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_206</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_213</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_224</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_230</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_285</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_293</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_602</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2005</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2009</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2011</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2014</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2055</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2111</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4012</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4125</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4126</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4249</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4306</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4307</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4313</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4322</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4323</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4324</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4325</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4338</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4367</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4700</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">28</subfield><subfield code="j">2023</subfield><subfield code="e">7190, p 7190</subfield></datafield></record></collection>
callnumber-first	Q - Science
author	Qin Pan
spellingShingle	Qin Pan misc QD241-441 misc ball milling misc Suzuki–Miyaura cross-coupling misc 1<i<H</i<-indazole misc PdO<sub<2</sub< nanoparticle misc silica gel misc Organic chemistry Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids
authorStr	Qin Pan
ppnlink_with_tag_str_mv	@@773@@(DE-627)311313132
format	electronic Article
delete_txt_mv	keep
author_role	aut aut aut aut aut aut aut aut aut aut
collection	DOAJ
remote_str	true
callnumber-label	QD241-441
illustrated	Not Illustrated
issn	14203049
topic_title	QD241-441 Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids ball milling Suzuki–Miyaura cross-coupling 1<i<H</i<-indazole PdO<sub<2</sub< nanoparticle silica gel
topic	misc QD241-441 misc ball milling misc Suzuki–Miyaura cross-coupling misc 1<i<H</i<-indazole misc PdO<sub<2</sub< nanoparticle misc silica gel misc Organic chemistry
topic_unstemmed	misc QD241-441 misc ball milling misc Suzuki–Miyaura cross-coupling misc 1<i<H</i<-indazole misc PdO<sub<2</sub< nanoparticle misc silica gel misc Organic chemistry
topic_browse	misc QD241-441 misc ball milling misc Suzuki–Miyaura cross-coupling misc 1<i<H</i<-indazole misc PdO<sub<2</sub< nanoparticle misc silica gel misc Organic chemistry
format_facet	Elektronische Aufsätze Aufsätze Elektronische Ressource
format_main_str_mv	Text Zeitschrift/Artikel
carriertype_str_mv	cr
hierarchy_parent_title	Molecules
hierarchy_parent_id	311313132
hierarchy_top_title	Molecules
isfreeaccess_txt	true
familylinks_str_mv	(DE-627)311313132 (DE-600)2008644-1
title	Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids
ctrlnum	(DE-627)DOAJ093098308 (DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b
title_full	Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids
author_sort	Qin Pan
journal	Molecules
journalStr	Molecules
callnumber-first-code	Q
lang_code	eng
isOA_bool	true
recordtype	marc
publishDateSort	2023
contenttype_str_mv	txt
author_browse	Qin Pan Yong Wu Aqun Zheng Xiangdong Wang Xiaoyong Li Wanqin Wang Min Gao Zainab Bibi Sidra Chaudhary Yang Sun
container_volume	28
class	QD241-441
format_se	Elektronische Aufsätze
author-letter	Qin Pan
doi_str_mv	10.3390/molecules28207190
author2-role	verfasserin
title_sort	mechanochemical synthesis of pdo<sub<2</sub< nanoparticles immobilized over silica gel for catalytic suzuki–miyaura cross-coupling reactions leading to the c-3 modification of 1<i<h</i<-indazole with phenylboronic acids
callnumber	QD241-441
title_auth	Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids
abstract	The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals.
abstractGer	The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals.
abstract_unstemmed	The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals.
collection_details	GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700
container_issue	7190, p 7190
title_short	Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids
url	https://doi.org/10.3390/molecules28207190 https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b https://www.mdpi.com/1420-3049/28/20/7190 https://doaj.org/toc/1420-3049
remote_bool	true
author2	Yong Wu Aqun Zheng Xiangdong Wang Xiaoyong Li Wanqin Wang Min Gao Zainab Bibi Sidra Chaudhary Yang Sun
author2Str	Yong Wu Aqun Zheng Xiangdong Wang Xiaoyong Li Wanqin Wang Min Gao Zainab Bibi Sidra Chaudhary Yang Sun
ppnlink	311313132
callnumber-subject	QD - Chemistry
mediatype_str_mv	c
isOA_txt	true
hochschulschrift_bool	false
doi_str	10.3390/molecules28207190
callnumber-a	QD241-441
up_date	2024-07-03T15:15:26.007Z
_version_	1803571404218564608
fullrecord_marcxml	<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000naa a22002652 4500</leader><controlfield tag="001">DOAJ093098308</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20240413215416.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">240413s2023 xx \|\|\|\|\|o 00\| \|\|eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.3390/molecules28207190</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)DOAJ093098308</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)DOAJaeb4943a4b6c4ffc853691bd5d1e098b</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="050" ind1=" " ind2="0"><subfield code="a">QD241-441</subfield></datafield><datafield tag="100" ind1="0" ind2=" "><subfield code="a">Qin Pan</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2023</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">The C-3 modification of 1<i<H</i<-indazole has produced active pharmaceuticals for the treatment of cancer and HIV. But, so far, this transformation has seemed less available, due to the lack of efficient C-C bond formation at the less reactive C-3 position. In this work, a series of silica gel-supported PdO<sub<2</sub< nanoparticles of 25–66 nm size were prepared by ball milling silica gel with divalent palladium precursors, and then employed as catalysts for the Suzuki–Miyaura cross-coupling of 1<i<H</i<-indazole derivative with phenylboronic acid. All the synthesized catalysts showed much higher cross-coupling yields than their palladium precursors, and could also be reused three times without losing high activity and selectivity in a toluene/water/ethanol mixed solvent. Although the palladium precursors showed an order of activity of PdCl<sub<2</sub<(dppf, 1,1′-bis(diphenylphosphino)ferrocene) < PdCl<sub<2</sub<(dtbpf, 1,1′-bis(di-<i<tert</i<-butylphosphino)ferrocene) < Pd(OAc, acetate)<sub<2</sub<, the synthesized catalysts showed an order of C1 (from Pd(OAc)<sub<2</sub<) < C3 (from PdCl<sub<2</sub<(dtbpf)) < C2 (from PdCl<sub<2</sub<(dppf)), which conformed to the orders of BET (Brunauer–Emmett–Teller) surface areas and acidities of these catalysts. Notably, the most inexpensive Pd(OAc)<sub<2</sub< can be used as a palladium precursor for the synthesis of the best catalyst through simple ball milling. This work provides a highly active and inexpensive series of catalysts for C-3 modification of 1<i<H</i<-indazole, which are significant for the large-scale production of 1<i<H</i<-indazole-based pharmaceuticals.</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">ball milling</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Suzuki–Miyaura cross-coupling</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">1<i<H</i<-indazole</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">PdO<sub<2</sub< nanoparticle</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">silica gel</subfield></datafield><datafield tag="653" ind1=" " ind2="0"><subfield code="a">Organic chemistry</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Yong Wu</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Aqun Zheng</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Xiangdong Wang</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Xiaoyong Li</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Wanqin Wang</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Min Gao</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Zainab Bibi</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Sidra Chaudhary</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="0" ind2=" "><subfield code="a">Yang Sun</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">In</subfield><subfield code="t">Molecules</subfield><subfield code="d">MDPI AG, 2003</subfield><subfield code="g">28(2023), 7190, p 7190</subfield><subfield code="w">(DE-627)311313132</subfield><subfield code="w">(DE-600)2008644-1</subfield><subfield code="x">14203049</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:28</subfield><subfield code="g">year:2023</subfield><subfield code="g">number:7190, p 7190</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doi.org/10.3390/molecules28207190</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://doaj.org/article/aeb4943a4b6c4ffc853691bd5d1e098b</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://www.mdpi.com/1420-3049/28/20/7190</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="u">https://doaj.org/toc/1420-3049</subfield><subfield code="y">Journal toc</subfield><subfield code="z">kostenfrei</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_DOAJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_20</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_22</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_23</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_39</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_40</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_60</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_63</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_65</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_70</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_73</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_95</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_105</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_151</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_161</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_170</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_206</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_213</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_224</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_230</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_285</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_293</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_602</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2005</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2009</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2011</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2014</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2055</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2111</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4012</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4125</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4126</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4249</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4306</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4307</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4313</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4322</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4323</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4324</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4325</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4338</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4367</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4700</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">28</subfield><subfield code="j">2023</subfield><subfield code="e">7190, p 7190</subfield></datafield></record></collection>
score	7.3996973

Nicht das Richtige dabei?

Schreiben Sie uns!

Mechanochemical Synthesis of PdO<sub<2</sub< Nanoparticles Immobilized over Silica Gel for Catalytic Suzuki–Miyaura Cross-Coupling Reactions Leading to the C-3 Modification of 1<i<H</i<-Indazole with Phenylboronic Acids

Nicht das Richtige dabei?

Zugang & Verfügbarkeit

Vorhandene Bände

Nicht das Richtige dabei?