Electrochemical Benzylic C-H Functionalization with Isocyanides

10 November 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)-H bonds with an isocyanide via an electrochemical process giving rise to structures which are encountered in several biologically relevant compounds and drugs. This transformation proceeds in mild conditions without the need of external oxidant and avoids the necessity to start from a prefunctionalized benzylic substrate or the deployment of the cation pool method. Anodic oxidation of the benzylic position and subsequent addition of the isocyanide leads to the formation of a C-C bond and to a nitrilium cation which hydrolysis leads to alpha-aryl acetamide derivatives, while elimination of a t-butyl cation delivers alpha-aryl acetonitrile derivatives.

Keywords

electrochemistry
benzylic oxidation
isocyanide

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