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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. ORCID: https://orcid.org/0000-0002-6453-7531 2021. Electrochemical oxidative Z-selective C(sp2)-H chlorination of acrylamides. Chemical Communications 57 (94) , pp. 12643-12646. 10.1039/D1CC05824J

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Additional Information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence
Publisher: Royal Society of Chemistry
ISSN: 1359-7345
Funders: EPSRC
Date of First Compliant Deposit: 16 November 2021
Date of Acceptance: 4 November 2021
Last Modified: 29 Nov 2022 10:08
URI: https://orca.cardiff.ac.uk/id/eprint/145547

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