Issue 10, 2017

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

Abstract

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.

Graphical abstract: α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration

Supplementary files

Article information

Article type
Edge Article
Submitted
15 May 2017
Accepted
02 Aug 2017
First published
04 Aug 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 6888-6892

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

X. Tang and A. Studer, Chem. Sci., 2017, 8, 6888 DOI: 10.1039/C7SC02175E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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