Metal‐Free Direct C−H Cyanation of Alkenes

A metal‐free and direct alkene C−H cyanation is described. Directing groups are not required and the mechanism involves electrophilic activation of the alkene by a cyano iodine(III) species generated in situ from a [bis(trifluoroacetoxy)iodo]arene and trimethylsilyl cyanide as the cyanide source. Th...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Xi, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6175092/
https://www.ncbi.nlm.nih.gov/pubmed/29995341
http://dx.doi.org/10.1002/anie.201807303
_version_ 1783361423469969408
author Wang, Xi
Studer, Armido
author_facet Wang, Xi
Studer, Armido
author_sort Wang, Xi
collection PubMed
description A metal‐free and direct alkene C−H cyanation is described. Directing groups are not required and the mechanism involves electrophilic activation of the alkene by a cyano iodine(III) species generated in situ from a [bis(trifluoroacetoxy)iodo]arene and trimethylsilyl cyanide as the cyanide source. This C−H functionalization can be conducted on gram scale, and for noncyclic 1,1‐ and 1,2‐disubstuted alkenes high stereoselectivity is achieved, thus rendering the method highly valuable.
format Online
Article
Text
id pubmed-6175092
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-61750922018-10-15 Metal‐Free Direct C−H Cyanation of Alkenes Wang, Xi Studer, Armido Angew Chem Int Ed Engl Communications A metal‐free and direct alkene C−H cyanation is described. Directing groups are not required and the mechanism involves electrophilic activation of the alkene by a cyano iodine(III) species generated in situ from a [bis(trifluoroacetoxy)iodo]arene and trimethylsilyl cyanide as the cyanide source. This C−H functionalization can be conducted on gram scale, and for noncyclic 1,1‐ and 1,2‐disubstuted alkenes high stereoselectivity is achieved, thus rendering the method highly valuable. John Wiley and Sons Inc. 2018-08-06 2018-09-03 /pmc/articles/PMC6175092/ /pubmed/29995341 http://dx.doi.org/10.1002/anie.201807303 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Wang, Xi
Studer, Armido
Metal‐Free Direct C−H Cyanation of Alkenes
title Metal‐Free Direct C−H Cyanation of Alkenes
title_full Metal‐Free Direct C−H Cyanation of Alkenes
title_fullStr Metal‐Free Direct C−H Cyanation of Alkenes
title_full_unstemmed Metal‐Free Direct C−H Cyanation of Alkenes
title_short Metal‐Free Direct C−H Cyanation of Alkenes
title_sort metal‐free direct c−h cyanation of alkenes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6175092/
https://www.ncbi.nlm.nih.gov/pubmed/29995341
http://dx.doi.org/10.1002/anie.201807303
work_keys_str_mv AT wangxi metalfreedirectchcyanationofalkenes
AT studerarmido metalfreedirectchcyanationofalkenes

Ejemplares similares