Electrochemical oxidative Z -selective C(sp2)-H chlorination of acrylamides

Harnedy, James, Hareram, Mishra Deepak, Tizzard, Graham J., Coles, Simon J. and Morrill, Louis C. (2021) Electrochemical oxidative Z -selective C(sp2)-H chlorination of acrylamides. Chemical Communications, 57 (94), 12643-12646. (doi:10.1039/d1cc05824j).

Record type: Article

Abstract

An electrochemical method for the oxidative Z-selective C(sp2)-H chlorination of acrylamides has been developed. This catalyst and organic oxidant free method is applicable across various substituted tertiary acrylamides, and provides access to a broad range of synthetically useful Z-β-chloroacrylamides in good yields (22 examples, 73% average yield). The orthogonal derivatization of the products was demonstrated through chemoselective transformations and the electrochemical process was performed on gram scale in flow.

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Accepted/In Press date: 4 November 2021

e-pub ahead of print date: 11 November 2021

Published date: 7 December 2021

Additional Information: Funding Information: We would like to thank Cardiff University for studentship funding for James Harnedy and the EPSRC for a standard research grant (EP/R006504/1). Publisher Copyright: © The Royal Society of Chemistry. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.