Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols

Aliphatic alcohols are common and bulk chemicals in organic synthesis. The site-selective functionalization of non-activated aliphatic alcohols is attractive but challenging. Herein, we report a silver-catalyzed δ-selective Csp(3)-H bond functionalization of abundant and inexpensive aliphatic alcoho...

Descripción completa

Detalles Bibliográficos
Autores principales: Zhu, Yuchao, Huang, Kaimeng, Pan, Jun, Qiu, Xu, Luo, Xiao, Qin, Qixue, Wei, Jialiang, Wen, Xiaojin, Zhang, Lizhi, Jiao, Ning
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6035238/
https://www.ncbi.nlm.nih.gov/pubmed/29980674
http://dx.doi.org/10.1038/s41467-018-05014-w
_version_ 1783338012996796416
author Zhu, Yuchao
Huang, Kaimeng
Pan, Jun
Qiu, Xu
Luo, Xiao
Qin, Qixue
Wei, Jialiang
Wen, Xiaojin
Zhang, Lizhi
Jiao, Ning
author_facet Zhu, Yuchao
Huang, Kaimeng
Pan, Jun
Qiu, Xu
Luo, Xiao
Qin, Qixue
Wei, Jialiang
Wen, Xiaojin
Zhang, Lizhi
Jiao, Ning
author_sort Zhu, Yuchao
collection PubMed
description Aliphatic alcohols are common and bulk chemicals in organic synthesis. The site-selective functionalization of non-activated aliphatic alcohols is attractive but challenging. Herein, we report a silver-catalyzed δ-selective Csp(3)-H bond functionalization of abundant and inexpensive aliphatic alcohols. Valuable oximonitrile substituted alcohols are easily obtained by using well-designed sulphonyl reagents under simple and mild conditions. This protocol realizes the challenging δ-selective C–C bond formation of simple alkanols.
format Online
Article
Text
id pubmed-6035238
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-60352382018-07-09 Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols Zhu, Yuchao Huang, Kaimeng Pan, Jun Qiu, Xu Luo, Xiao Qin, Qixue Wei, Jialiang Wen, Xiaojin Zhang, Lizhi Jiao, Ning Nat Commun Article Aliphatic alcohols are common and bulk chemicals in organic synthesis. The site-selective functionalization of non-activated aliphatic alcohols is attractive but challenging. Herein, we report a silver-catalyzed δ-selective Csp(3)-H bond functionalization of abundant and inexpensive aliphatic alcohols. Valuable oximonitrile substituted alcohols are easily obtained by using well-designed sulphonyl reagents under simple and mild conditions. This protocol realizes the challenging δ-selective C–C bond formation of simple alkanols. Nature Publishing Group UK 2018-07-06 /pmc/articles/PMC6035238/ /pubmed/29980674 http://dx.doi.org/10.1038/s41467-018-05014-w Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Zhu, Yuchao
Huang, Kaimeng
Pan, Jun
Qiu, Xu
Luo, Xiao
Qin, Qixue
Wei, Jialiang
Wen, Xiaojin
Zhang, Lizhi
Jiao, Ning
Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols
title Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols
title_full Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols
title_fullStr Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols
title_full_unstemmed Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols
title_short Silver-catalyzed remote Csp(3)-H functionalization of aliphatic alcohols
title_sort silver-catalyzed remote csp(3)-h functionalization of aliphatic alcohols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6035238/
https://www.ncbi.nlm.nih.gov/pubmed/29980674
http://dx.doi.org/10.1038/s41467-018-05014-w
work_keys_str_mv AT zhuyuchao silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT huangkaimeng silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT panjun silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT qiuxu silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT luoxiao silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT qinqixue silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT weijialiang silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT wenxiaojin silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT zhanglizhi silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols
AT jiaoning silvercatalyzedremotecsp3hfunctionalizationofaliphaticalcohols

Ejemplares similares