α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration

Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented. These cascades proceed via electron-catalysis and comprise a radical 1,4- or 1,5-alkynyl migration from tertiary propargylic alcoholates to secondary or tertiary C-radicals as the...

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Detalles Bibliográficos
Autores principales: Tang, Xinjun, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5637125/
https://www.ncbi.nlm.nih.gov/pubmed/29147514
http://dx.doi.org/10.1039/c7sc02175e
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author Tang, Xinjun
Studer, Armido
author_facet Tang, Xinjun
Studer, Armido
author_sort Tang, Xinjun
collection PubMed
description Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented. These cascades proceed via electron-catalysis and comprise a radical 1,4- or 1,5-alkynyl migration from tertiary propargylic alcoholates to secondary or tertiary C-radicals as the key step. Alkynyl migration leads to a ketyl radical anion that sustains the chain as a single electron transfer reducing reagent.
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spelling pubmed-56371252017-11-16 α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration Tang, Xinjun Studer, Armido Chem Sci Chemistry Transition metal-free radical α-perfluoroalkylation with concomitant β-alkynylation of unactivated alkenes is presented. These cascades proceed via electron-catalysis and comprise a radical 1,4- or 1,5-alkynyl migration from tertiary propargylic alcoholates to secondary or tertiary C-radicals as the key step. Alkynyl migration leads to a ketyl radical anion that sustains the chain as a single electron transfer reducing reagent. Royal Society of Chemistry 2017-10-01 2017-08-04 /pmc/articles/PMC5637125/ /pubmed/29147514 http://dx.doi.org/10.1039/c7sc02175e Text en This journal is © The Royal Society of Chemistry 2017 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
Tang, Xinjun
Studer, Armido
α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
title α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
title_full α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
title_fullStr α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
title_full_unstemmed α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
title_short α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
title_sort α-perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5637125/
https://www.ncbi.nlm.nih.gov/pubmed/29147514
http://dx.doi.org/10.1039/c7sc02175e
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