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 5 2017
Accepted
02 8 2017
First published
04 8 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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