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Electrochemical alkene azidocyanation via 1,4-nitrile migration†
Alex C. Seastram,Mishra Deepak Hareram,Thomas M. B. Knight,Louis C. Morrill
Chemical Communications Pub Date : 07/13/2022 00:00:00 , DOI:10.1039/D2CC02958H
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.

Graphical abstract: Electrochemical alkene azidocyanation via 1,4-nitrile migration
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