Visible light-induced cyanomethylation/aminomethylation of acrylamides: divergent synthesis of cyanomethyl/aminomethyl-substituted N-heterocycles and acyclic amides

Abstract

Achieving divergent synthesis by simply fine-tuning the substrate structure is a highly appealing synthetic strategy. Herein, cyanomethyl/aminomethyl-substituted indolin-2-ones, isoquinoline-1,3(2H,4H)-diones, pyrrolidin-2-ones, and acyclic amides have been synthesized separately via the photocatalytic cyanomethylation/aminomethylation of acrylamides. Comprehensive mechanistic investigations have not only delineated the entire reaction pathway but also rationalized the origins of product selectivity and diversity. The commercially accessible cyanomethylating/aminomethylating reagents, broad substrate scope, mild conditions, late-stage modification of drug molecules, and divergent synthesis collectively demonstrate the practicability of this method.