Synthesis of tetrahydroquinoline derivatives via electrochemical hydrocyanomethylation or hydrogenation of quinolines with MeCN

Abstract

A series of tetrahydroquinoline derivatives were selectively synthesized at room temperature via electrochemical hydrocyanomethylation of quinoline skeletons using acetonitrile as both a hydrogen source and a cyanomethyl precursor. When a bulky substituent was present at the C2 position, hydrogenation of quinoline derivatives dominated. Furthermore, a deuterium labeling experiment revealed that protons were derived from acetonitrile. This method features mild conditions, high efficiency, wide substrate scope, and good functional group tolerance.