Copper-catalyzed cyanation of heterocycle C–H bonds with ethyl(ethoxymethylene)cyanoacetate as a cyanating agent and its mechanism?

Organic Chemistry Frontiers Pub Date: 2018-04-26 DOI: 10.1039/C8QO00322J

Abstract

A method for copper-catalyzed cyanation of heterocycles with ethyl(ethoxymethylene)cyanoacetate as a nontoxic and easily available cyanating agent via C–H bond activation has been developed. This transformation could proceed smoothly in the presence of di-tert-butyl peroxide (DTBP) with a wide substrate scope under ligand-free conditions, providing a safe and efficient route for the synthesis of a wide range of (hetero)aryl nitriles. Mechanistic details were also described.

Graphical abstract: Copper-catalyzed cyanation of heterocycle C–H bonds with ethyl(ethoxymethylene)cyanoacetate as a cyanating agent and its mechanism
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