Cargando…
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...
Autores principales: | , , , , , |
---|---|
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 |
_version_ | 1783308112511369216 |
---|---|
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. |
format | Online Article Text |
id | pubmed-5861525 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT wangchao oxalylamideassistedpalladiumcatalyzedsynthesisofpyrrolidonesviacarbonylationofgcsp3hbondsofaliphaticaminesubstrates AT zhangli oxalylamideassistedpalladiumcatalyzedsynthesisofpyrrolidonesviacarbonylationofgcsp3hbondsofaliphaticaminesubstrates AT chenchangpeng oxalylamideassistedpalladiumcatalyzedsynthesisofpyrrolidonesviacarbonylationofgcsp3hbondsofaliphaticaminesubstrates AT hanjian oxalylamideassistedpalladiumcatalyzedsynthesisofpyrrolidonesviacarbonylationofgcsp3hbondsofaliphaticaminesubstrates AT yaoyingming oxalylamideassistedpalladiumcatalyzedsynthesisofpyrrolidonesviacarbonylationofgcsp3hbondsofaliphaticaminesubstrates AT zhaoyingsheng oxalylamideassistedpalladiumcatalyzedsynthesisofpyrrolidonesviacarbonylationofgcsp3hbondsofaliphaticaminesubstrates |