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Electrochemical alkene azidocyanation via 1,4-nitrile migration

Seastram, Alex C., Hareram, Mishra Deepak, Knight, Thomas M. B. and Morrill, Louis C. 2022. Electrochemical alkene azidocyanation via 1,4-nitrile migration. Chemical Communications 10.1039/D2CC02958H

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Abstract

An electrochemical method for the azidocyanation of alkenes via 1,4-nitrile migration has been developed. This organic oxidant free method is applicable across various alkene containing cyanohydrins, and provides access to a broad range of synthetically useful 1,2-azidonitriles (28 examples). This methodology was extended to an electrochemical alkene sulfonylcyanation procedure, as well as to access a trifunctionalized hexanenitrile from a malononitrile starting material. The orthogonal derivatization of the products was also demonstrated through chemoselective transformations.

Item Type: Article
Date Type: Published Online
Status: In Press
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: 26 July 2022
Date of Acceptance: 6 July 2022
Last Modified: 02 Aug 2022 01:07
URI: https://orca.cardiff.ac.uk/id/eprint/151466

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