Issue 7, 2018

Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes

Abstract

Stereoselective additions of highly functionalized reagents to available unsaturated hydrocarbons are an attractive synthetic tool due to their high atom economy, modularity, and rapid generation of complexity. We report efficient cobalt-catalyzed (E)-halofluoroalkylations of alkynes/alkenes that enable the construction of densely functionalized, stereodefined fluorinated hydrocarbons. The mild conditions (2 mol% cat., 20 °C, acetone/water, 3 h) tolerate various functional groups, i.e. halides, alcohols, aldehydes, nitriles, esters, and heteroarenes. This reaction is the first example of a highly stereoselective cobalt-catalyzed halo-fluoroalkylation. Unlike related cobalt-catalyzed reductive couplings and Heck-type reactions, it operates via a radical chain mechanism involving terminal halogen atom transfer which obviates the need for a stoichiometric sacrificial reductant.

Graphical abstract: Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes

Supplementary files

Article information

Article type
Edge Article
Submitted
16 Nov 2017
Accepted
03 Jan 2018
First published
05 Jan 2018
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., 2018,9, 1795-1802

Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes

G. Wu and A. Jacobi von Wangelin, Chem. Sci., 2018, 9, 1795 DOI: 10.1039/C7SC04916A

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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