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Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates

The first Pd-catalyzed regioselective γ-carbonylation of oxalyl amide protected aliphatic amines with carbon monoxide leading to synthesis of pyrrolidones has been developed. Both γ-methyl and cyclopropyl methylene C–H bonds are well activated to obtain the corresponding pyrrolidones in moderate to...

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Detalles Bibliográficos
Autores principales: Wang, Chao, Zhang, Li, Chen, Changpeng, Han, Jian, Yao, Yingming, Zhao, Yingsheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5861525/
https://www.ncbi.nlm.nih.gov/pubmed/29619163
http://dx.doi.org/10.1039/c5sc00519a
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author Wang, Chao
Zhang, Li
Chen, Changpeng
Han, Jian
Yao, Yingming
Zhao, Yingsheng
author_facet Wang, Chao
Zhang, Li
Chen, Changpeng
Han, Jian
Yao, Yingming
Zhao, Yingsheng
author_sort Wang, Chao
collection PubMed
description The first Pd-catalyzed regioselective γ-carbonylation of oxalyl amide protected aliphatic amines with carbon monoxide leading to synthesis of pyrrolidones has been developed. Both γ-methyl and cyclopropyl methylene C–H bonds are well activated to obtain the corresponding pyrrolidones in moderate to excellent yields. The role of 3-(trifluoromethyl)benzoic acid as an additive is critical as it helps in stabilizing the palladium intermediate formed during the catalytic cycle. The reaction scope is extended to benzylamine and allyl amine derivatives, thereby affording the corresponding products in good to excellent yields.
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spelling pubmed-58615252018-04-04 Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates Wang, Chao Zhang, Li Chen, Changpeng Han, Jian Yao, Yingming Zhao, Yingsheng Chem Sci Chemistry The first Pd-catalyzed regioselective γ-carbonylation of oxalyl amide protected aliphatic amines with carbon monoxide leading to synthesis of pyrrolidones has been developed. Both γ-methyl and cyclopropyl methylene C–H bonds are well activated to obtain the corresponding pyrrolidones in moderate to excellent yields. The role of 3-(trifluoromethyl)benzoic acid as an additive is critical as it helps in stabilizing the palladium intermediate formed during the catalytic cycle. The reaction scope is extended to benzylamine and allyl amine derivatives, thereby affording the corresponding products in good to excellent yields. Royal Society of Chemistry 2015-08-01 2015-05-19 /pmc/articles/PMC5861525/ /pubmed/29619163 http://dx.doi.org/10.1039/c5sc00519a Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Wang, Chao
Zhang, Li
Chen, Changpeng
Han, Jian
Yao, Yingming
Zhao, Yingsheng
Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
title Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
title_full Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
title_fullStr Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
title_full_unstemmed Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
title_short Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp(3))–H bonds of aliphatic amine substrates
title_sort oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-c(sp(3))–h bonds of aliphatic amine substrates
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5861525/
https://www.ncbi.nlm.nih.gov/pubmed/29619163
http://dx.doi.org/10.1039/c5sc00519a
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