Electrochemically enabled decyanative C(sp3)-H oxygenation of N-cyanomethylamines to formamides

Org Biomol Chem. 2023 Apr 5;21(14):2917-2921. doi: 10.1039/d3ob00313b.

Abstract

Selective oxygenation of C(sp3)-H bonds adjacent to nitrogen atoms is a highly attractive strategy for synthesizing various formamide derivatives while preserving the substrate skeletons. Herein, an environmentally benign electrochemically enabled decyanative C(sp3)-H oxygenation of N-cyanomethylamines using H2O as a carbonyl oxygen atom source is described, leading to the synthesis of a large class of formamides in good to excellent yields with a broad substrate scope under metal- and oxidant-free conditions. This electrochemical technology highlights the facile incorporation of N-formyl into some important bioactive molecules.