Issue 7, 2018

Stereoselective cobalt-catalyzed halofluoroalkylation of alkynes


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

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Article information

Article type
Edge Article
16 Nov 2017
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

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