Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical

A pyridine-boryl radical promoted reductive coupling reaction of aldehydes with 1,1-diarylethylenes has been established via a combination of computational and experimental studies. Density functional theory calculations and control experiments suggest that the ketyl radical from the addition of the...

Descripción completa

Detalles Bibliográficos
Autores principales: Cao, Jia, Wang, Guoqiang, Gao, Liuzhou, Cheng, Xu, Li, Shuhua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5933217/
https://www.ncbi.nlm.nih.gov/pubmed/29780496
http://dx.doi.org/10.1039/c7sc05225a
_version_ 1783319936845742080
author Cao, Jia
Wang, Guoqiang
Gao, Liuzhou
Cheng, Xu
Li, Shuhua
author_facet Cao, Jia
Wang, Guoqiang
Gao, Liuzhou
Cheng, Xu
Li, Shuhua
author_sort Cao, Jia
collection PubMed
description A pyridine-boryl radical promoted reductive coupling reaction of aldehydes with 1,1-diarylethylenes has been established via a combination of computational and experimental studies. Density functional theory calculations and control experiments suggest that the ketyl radical from the addition of the pyridine-boryl radical to aldehydes is the key intermediate for this C–C bond formation reaction. This metal-free reductive coupling reaction features a broad substrate scope and good functional compatibility.
format Online
Article
Text
id pubmed-5933217
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-59332172018-05-18 Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical Cao, Jia Wang, Guoqiang Gao, Liuzhou Cheng, Xu Li, Shuhua Chem Sci Chemistry A pyridine-boryl radical promoted reductive coupling reaction of aldehydes with 1,1-diarylethylenes has been established via a combination of computational and experimental studies. Density functional theory calculations and control experiments suggest that the ketyl radical from the addition of the pyridine-boryl radical to aldehydes is the key intermediate for this C–C bond formation reaction. This metal-free reductive coupling reaction features a broad substrate scope and good functional compatibility. Royal Society of Chemistry 2018-02-28 /pmc/articles/PMC5933217/ /pubmed/29780496 http://dx.doi.org/10.1039/c7sc05225a Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Cao, Jia
Wang, Guoqiang
Gao, Liuzhou
Cheng, Xu
Li, Shuhua
Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
title Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
title_full Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
title_fullStr Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
title_full_unstemmed Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
title_short Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
title_sort organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5933217/
https://www.ncbi.nlm.nih.gov/pubmed/29780496
http://dx.doi.org/10.1039/c7sc05225a
work_keys_str_mv AT caojia organocatalyticreductivecouplingofaldehydeswith11diarylethylenesusinganinsitugeneratedpyridineborylradical
AT wangguoqiang organocatalyticreductivecouplingofaldehydeswith11diarylethylenesusinganinsitugeneratedpyridineborylradical
AT gaoliuzhou organocatalyticreductivecouplingofaldehydeswith11diarylethylenesusinganinsitugeneratedpyridineborylradical
AT chengxu organocatalyticreductivecouplingofaldehydeswith11diarylethylenesusinganinsitugeneratedpyridineborylradical
AT lishuhua organocatalyticreductivecouplingofaldehydeswith11diarylethylenesusinganinsitugeneratedpyridineborylradical

Ejemplares similares