Copper-catalyzed propargylic C–H functionalization for allene syntheses

Allenenitriles bearing different synthetically versatile functional groups have been prepared smoothly from 5-alkynyl fluorosulfonamides in decent yields with an excellent chemo- and regio-selectivity under redox neutral conditions. The resulting allenenitriles can be readily converted to useful fun...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhang, Dongjie, Fan, Junjie, Shi, Yaqi, Huang, Yankai, Fu, Chunling, Wu, Xiaoyan, Ma, Shengming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10466309/
https://www.ncbi.nlm.nih.gov/pubmed/37655026
http://dx.doi.org/10.1039/d3sc01501g
_version_ 1785098854074417152
author Zhang, Dongjie
Fan, Junjie
Shi, Yaqi
Huang, Yankai
Fu, Chunling
Wu, Xiaoyan
Ma, Shengming
author_facet Zhang, Dongjie
Fan, Junjie
Shi, Yaqi
Huang, Yankai
Fu, Chunling
Wu, Xiaoyan
Ma, Shengming
author_sort Zhang, Dongjie
collection PubMed
description Allenenitriles bearing different synthetically versatile functional groups have been prepared smoothly from 5-alkynyl fluorosulfonamides in decent yields with an excellent chemo- and regio-selectivity under redox neutral conditions. The resulting allenenitriles can be readily converted to useful functionalized heterocycles. Based on mechanistic study, it is confirmed that this is the first example of radical-based non-activated propargylic C–H functionalization for allene syntheses.
format Online
Article
Text
id pubmed-10466309
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-104663092023-08-31 Copper-catalyzed propargylic C–H functionalization for allene syntheses Zhang, Dongjie Fan, Junjie Shi, Yaqi Huang, Yankai Fu, Chunling Wu, Xiaoyan Ma, Shengming Chem Sci Chemistry Allenenitriles bearing different synthetically versatile functional groups have been prepared smoothly from 5-alkynyl fluorosulfonamides in decent yields with an excellent chemo- and regio-selectivity under redox neutral conditions. The resulting allenenitriles can be readily converted to useful functionalized heterocycles. Based on mechanistic study, it is confirmed that this is the first example of radical-based non-activated propargylic C–H functionalization for allene syntheses. The Royal Society of Chemistry 2023-08-09 /pmc/articles/PMC10466309/ /pubmed/37655026 http://dx.doi.org/10.1039/d3sc01501g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zhang, Dongjie
Fan, Junjie
Shi, Yaqi
Huang, Yankai
Fu, Chunling
Wu, Xiaoyan
Ma, Shengming
Copper-catalyzed propargylic C–H functionalization for allene syntheses
title Copper-catalyzed propargylic C–H functionalization for allene syntheses
title_full Copper-catalyzed propargylic C–H functionalization for allene syntheses
title_fullStr Copper-catalyzed propargylic C–H functionalization for allene syntheses
title_full_unstemmed Copper-catalyzed propargylic C–H functionalization for allene syntheses
title_short Copper-catalyzed propargylic C–H functionalization for allene syntheses
title_sort copper-catalyzed propargylic c–h functionalization for allene syntheses
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10466309/
https://www.ncbi.nlm.nih.gov/pubmed/37655026
http://dx.doi.org/10.1039/d3sc01501g
work_keys_str_mv AT zhangdongjie coppercatalyzedpropargylicchfunctionalizationforallenesyntheses
AT fanjunjie coppercatalyzedpropargylicchfunctionalizationforallenesyntheses
AT shiyaqi coppercatalyzedpropargylicchfunctionalizationforallenesyntheses
AT huangyankai coppercatalyzedpropargylicchfunctionalizationforallenesyntheses
AT fuchunling coppercatalyzedpropargylicchfunctionalizationforallenesyntheses
AT wuxiaoyan coppercatalyzedpropargylicchfunctionalizationforallenesyntheses
AT mashengming coppercatalyzedpropargylicchfunctionalizationforallenesyntheses

Ejemplares similares