HOTf-Catalyzed Alkyl-Heck-type Reaction

Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions ar...
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Autor*in:	Huan Zhou [verfasserIn] Liang Ge [verfasserIn] Jinshuai Song [verfasserIn] Wujun Jian [verfasserIn] Yajun Li [verfasserIn] Chunsen Li [verfasserIn] Hongli Bao [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Übergeordnetes Werk:	In: iScience - Elsevier, 2019, 3(2018), Seite 255-263
Übergeordnetes Werk:	volume:3 ; year:2018 ; pages:255-263

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.1016/j.isci.2018.04.020

Katalog-ID:	DOAJ052621243

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520			\|a Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis
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matchkey_str	article:25890042:2018----::ofaayeakleky
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publishDate	2018
allfields	10.1016/j.isci.2018.04.020 doi (DE-627)DOAJ052621243 (DE-599)DOAJ897e5e2e4d794faebfd239fe63c27cde DE-627 ger DE-627 rakwb eng Huan Zhou verfasserin aut HOTf-Catalyzed Alkyl-Heck-type Reaction 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis Science Q Liang Ge verfasserin aut Jinshuai Song verfasserin aut Wujun Jian verfasserin aut Yajun Li verfasserin aut Chunsen Li verfasserin aut Hongli Bao verfasserin aut In iScience Elsevier, 2019 3(2018), Seite 255-263 (DE-627)1019532106 25890042 nnns volume:3 year:2018 pages:255-263 https://doi.org/10.1016/j.isci.2018.04.020 kostenfrei https://doaj.org/article/897e5e2e4d794faebfd239fe63c27cde kostenfrei http://www.sciencedirect.com/science/article/pii/S258900421830052X kostenfrei https://doaj.org/toc/2589-0042 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 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_171 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2110 GBV_ILN_2112 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4251 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_4326 GBV_ILN_4333 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 3 2018 255-263
spelling	10.1016/j.isci.2018.04.020 doi (DE-627)DOAJ052621243 (DE-599)DOAJ897e5e2e4d794faebfd239fe63c27cde DE-627 ger DE-627 rakwb eng Huan Zhou verfasserin aut HOTf-Catalyzed Alkyl-Heck-type Reaction 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis Science Q Liang Ge verfasserin aut Jinshuai Song verfasserin aut Wujun Jian verfasserin aut Yajun Li verfasserin aut Chunsen Li verfasserin aut Hongli Bao verfasserin aut In iScience Elsevier, 2019 3(2018), Seite 255-263 (DE-627)1019532106 25890042 nnns volume:3 year:2018 pages:255-263 https://doi.org/10.1016/j.isci.2018.04.020 kostenfrei https://doaj.org/article/897e5e2e4d794faebfd239fe63c27cde kostenfrei http://www.sciencedirect.com/science/article/pii/S258900421830052X kostenfrei https://doaj.org/toc/2589-0042 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 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_171 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2110 GBV_ILN_2112 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4251 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_4326 GBV_ILN_4333 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 3 2018 255-263
allfields_unstemmed	10.1016/j.isci.2018.04.020 doi (DE-627)DOAJ052621243 (DE-599)DOAJ897e5e2e4d794faebfd239fe63c27cde DE-627 ger DE-627 rakwb eng Huan Zhou verfasserin aut HOTf-Catalyzed Alkyl-Heck-type Reaction 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis Science Q Liang Ge verfasserin aut Jinshuai Song verfasserin aut Wujun Jian verfasserin aut Yajun Li verfasserin aut Chunsen Li verfasserin aut Hongli Bao verfasserin aut In iScience Elsevier, 2019 3(2018), Seite 255-263 (DE-627)1019532106 25890042 nnns volume:3 year:2018 pages:255-263 https://doi.org/10.1016/j.isci.2018.04.020 kostenfrei https://doaj.org/article/897e5e2e4d794faebfd239fe63c27cde kostenfrei http://www.sciencedirect.com/science/article/pii/S258900421830052X kostenfrei https://doaj.org/toc/2589-0042 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 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_171 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2110 GBV_ILN_2112 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4251 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_4326 GBV_ILN_4333 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 3 2018 255-263
allfieldsGer	10.1016/j.isci.2018.04.020 doi (DE-627)DOAJ052621243 (DE-599)DOAJ897e5e2e4d794faebfd239fe63c27cde DE-627 ger DE-627 rakwb eng Huan Zhou verfasserin aut HOTf-Catalyzed Alkyl-Heck-type Reaction 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis Science Q Liang Ge verfasserin aut Jinshuai Song verfasserin aut Wujun Jian verfasserin aut Yajun Li verfasserin aut Chunsen Li verfasserin aut Hongli Bao verfasserin aut In iScience Elsevier, 2019 3(2018), Seite 255-263 (DE-627)1019532106 25890042 nnns volume:3 year:2018 pages:255-263 https://doi.org/10.1016/j.isci.2018.04.020 kostenfrei https://doaj.org/article/897e5e2e4d794faebfd239fe63c27cde kostenfrei http://www.sciencedirect.com/science/article/pii/S258900421830052X kostenfrei https://doaj.org/toc/2589-0042 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 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_171 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2110 GBV_ILN_2112 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4251 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_4326 GBV_ILN_4333 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 3 2018 255-263
allfieldsSound	10.1016/j.isci.2018.04.020 doi (DE-627)DOAJ052621243 (DE-599)DOAJ897e5e2e4d794faebfd239fe63c27cde DE-627 ger DE-627 rakwb eng Huan Zhou verfasserin aut HOTf-Catalyzed Alkyl-Heck-type Reaction 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis Science Q Liang Ge verfasserin aut Jinshuai Song verfasserin aut Wujun Jian verfasserin aut Yajun Li verfasserin aut Chunsen Li verfasserin aut Hongli Bao verfasserin aut In iScience Elsevier, 2019 3(2018), Seite 255-263 (DE-627)1019532106 25890042 nnns volume:3 year:2018 pages:255-263 https://doi.org/10.1016/j.isci.2018.04.020 kostenfrei https://doaj.org/article/897e5e2e4d794faebfd239fe63c27cde kostenfrei http://www.sciencedirect.com/science/article/pii/S258900421830052X kostenfrei https://doaj.org/toc/2589-0042 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 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_171 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2110 GBV_ILN_2112 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4251 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_4326 GBV_ILN_4333 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 3 2018 255-263
language	English
source	In iScience 3(2018), Seite 255-263 volume:3 year:2018 pages:255-263
sourceStr	In iScience 3(2018), Seite 255-263 volume:3 year:2018 pages:255-263
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Science Q
isfreeaccess_bool	true
container_title	iScience
authorswithroles_txt_mv	Huan Zhou @@aut@@ Liang Ge @@aut@@ Jinshuai Song @@aut@@ Wujun Jian @@aut@@ Yajun Li @@aut@@ Chunsen Li @@aut@@ Hongli Bao @@aut@@
publishDateDaySort_date	2018-01-01T00:00:00Z
hierarchy_top_id	1019532106
id	DOAJ052621243
language_de	englisch
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author	Huan Zhou
spellingShingle	Huan Zhou misc Science misc Q HOTf-Catalyzed Alkyl-Heck-type Reaction
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topic_title	HOTf-Catalyzed Alkyl-Heck-type Reaction
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title	HOTf-Catalyzed Alkyl-Heck-type Reaction
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title_full	HOTf-Catalyzed Alkyl-Heck-type Reaction
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title_sort	hotf-catalyzed alkyl-heck-type reaction
title_auth	HOTf-Catalyzed Alkyl-Heck-type Reaction
abstract	Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis
abstractGer	Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis
abstract_unstemmed	Summary: The Heck reaction, along with other cross-coupling reactions, led to a revolution in organic chemistry. In the last 50 years, metal-catalyzed, photo-induced, or base-mediated Heck and Heck-type reactions have been elegantly developed. Brønsted acid-catalyzed Heck (or Heck-type) reactions are still unknown, however. By introducing alkyl peroxides as the key intermediates, primary, secondary, and tertiary aliphatic carboxylic acids are therefore applied here in a one-pot Brønsted acid-catalyzed Heck-type reaction, to deliver E-alkenes exclusively in most cases. The use of HOTf is vital to the reaction, whose mechanism is supported by both experimental and computational results. This method can be expanded to the direct alkylation of complex natural products. : Organic Synthesis; Organic Chemistry Methods; Natural Product Synthesis Subject Areas: Organic Synthesis, Organic Chemistry Methods, Natural Product Synthesis
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title_short	HOTf-Catalyzed Alkyl-Heck-type Reaction
url	https://doi.org/10.1016/j.isci.2018.04.020 https://doaj.org/article/897e5e2e4d794faebfd239fe63c27cde http://www.sciencedirect.com/science/article/pii/S258900421830052X https://doaj.org/toc/2589-0042
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up_date	2024-07-04T01:45:37.578Z
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score	7.3978004

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HOTf-Catalyzed Alkyl-Heck-type Reaction

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