Selective Electrochemical Halogenation of Functionalized Quinolone

J Org Chem. 2023 Sep 15;88(18):12958-12970. doi: 10.1021/acs.joc.3c00876. Epub 2023 Aug 24.

Abstract

This work describes an effective C3-H halogenation of quinoline-4(1H)-ones under electrochemical conditions, in which potassium halides serve as both halogenating agents and electrolytes. The protocol provides expedient access to different halogenated quinoline-4(1H)-ones with unique regioselectivity, broad substrate scope, and gram-scale synthesis employing convenient, environmentally friendly electrolysis, in an undivided cell. Mechanism studies have shown that halogen radicals can promote the activation of N-H bonds in quinolones.