A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations

Traditional, established palladium cross-coupling procedures are widely applied in complex molecule synthesis; however, there is a significant disadvantage in the requirement for pre-functionalised substrates (commonly halides/triflates). Direct C–H activation protocols provide the opportunity for a...
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Autor*in:	Andrew Kenny [verfasserIn] Alba Pisarello [verfasserIn] Arron Bird [verfasserIn] Paula G. Chirila [verfasserIn] Alex Hamilton [verfasserIn] Christopher J. Whiteoak [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	acetanilides alkylation C–H activation cobalt catalysis DFT studies

Übergeordnetes Werk:	In: Beilstein Journal of Organic Chemistry - Beilstein-Institut, 2005, 14(2018), 1, Seite 2366-2374
Übergeordnetes Werk:	volume:14 ; year:2018 ; number:1 ; pages:2366-2374

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3762/bjoc.14.212

Katalog-ID:	DOAJ071875891

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source	In Beilstein Journal of Organic Chemistry 14(2018), 1, Seite 2366-2374 volume:14 year:2018 number:1 pages:2366-2374
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authorswithroles_txt_mv	Andrew Kenny @@aut@@ Alba Pisarello @@aut@@ Arron Bird @@aut@@ Paula G. Chirila @@aut@@ Alex Hamilton @@aut@@ Christopher J. Whiteoak @@aut@@
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callnumber-first	Q - Science
author	Andrew Kenny
spellingShingle	Andrew Kenny misc QD241-441 misc acetanilides misc alkylation misc C–H activation misc cobalt catalysis misc DFT studies misc Science misc Q misc Organic chemistry A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations
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topic_title	QD241-441 A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations acetanilides alkylation C–H activation cobalt catalysis DFT studies
topic	misc QD241-441 misc acetanilides misc alkylation misc C–H activation misc cobalt catalysis misc DFT studies misc Science misc Q misc Organic chemistry
topic_unstemmed	misc QD241-441 misc acetanilides misc alkylation misc C–H activation misc cobalt catalysis misc DFT studies misc Science misc Q misc Organic chemistry
topic_browse	misc QD241-441 misc acetanilides misc alkylation misc C–H activation misc cobalt catalysis misc DFT studies misc Science misc Q misc Organic chemistry
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title	A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations
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title_full	A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations
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title_sort	challenging redox neutral cp*co(iii)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through dft calculations
callnumber	QD241-441
title_auth	A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations
abstract	Traditional, established palladium cross-coupling procedures are widely applied in complex molecule synthesis; however, there is a significant disadvantage in the requirement for pre-functionalised substrates (commonly halides/triflates). Direct C–H activation protocols provide the opportunity for a novel approach to synthesis, although this field is still in its relative infancy and often transferability between substrate classes remains unresolved and limitations not fully understood. This study focuses on the translation of an established Cp*Co(III)-catalysed alkylation of benzamides to related acetanilides using 3-buten-2-one as coupling partner. The developed procedure provides a wide substrate scope in terms of substituted acetanilides, although the optimised conditions were found to be more forcing than those for the corresponding benzamide substrates. Interestingly, density functional theory (DFT) studies reveal that the major impediment in the mechanism is not the C–H activation step, but instead and unexpectedly, effective competition with more stable compounds (resting states) not involved in the catalytic cycle.
abstractGer	Traditional, established palladium cross-coupling procedures are widely applied in complex molecule synthesis; however, there is a significant disadvantage in the requirement for pre-functionalised substrates (commonly halides/triflates). Direct C–H activation protocols provide the opportunity for a novel approach to synthesis, although this field is still in its relative infancy and often transferability between substrate classes remains unresolved and limitations not fully understood. This study focuses on the translation of an established Cp*Co(III)-catalysed alkylation of benzamides to related acetanilides using 3-buten-2-one as coupling partner. The developed procedure provides a wide substrate scope in terms of substituted acetanilides, although the optimised conditions were found to be more forcing than those for the corresponding benzamide substrates. Interestingly, density functional theory (DFT) studies reveal that the major impediment in the mechanism is not the C–H activation step, but instead and unexpectedly, effective competition with more stable compounds (resting states) not involved in the catalytic cycle.
abstract_unstemmed	Traditional, established palladium cross-coupling procedures are widely applied in complex molecule synthesis; however, there is a significant disadvantage in the requirement for pre-functionalised substrates (commonly halides/triflates). Direct C–H activation protocols provide the opportunity for a novel approach to synthesis, although this field is still in its relative infancy and often transferability between substrate classes remains unresolved and limitations not fully understood. This study focuses on the translation of an established Cp*Co(III)-catalysed alkylation of benzamides to related acetanilides using 3-buten-2-one as coupling partner. The developed procedure provides a wide substrate scope in terms of substituted acetanilides, although the optimised conditions were found to be more forcing than those for the corresponding benzamide substrates. Interestingly, density functional theory (DFT) studies reveal that the major impediment in the mechanism is not the C–H activation step, but instead and unexpectedly, effective competition with more stable compounds (resting states) not involved in the catalytic cycle.
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title_short	A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations
url	https://doi.org/10.3762/bjoc.14.212 https://doaj.org/article/002e7f83b1514565807048a13712cd8e https://doaj.org/toc/1860-5397
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up_date	2024-07-03T22:38:57.721Z
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A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations

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