Activation of Aryl and Alkyl Halides Enabled by Strong Photoreduction Potentials of a Hantzsch Ester/Cs2CO3 System

J Org Chem. 2024 Jan 5;89(1):599-604. doi: 10.1021/acs.joc.3c02320. Epub 2023 Dec 19.

Abstract

We disclose herein a light-induced Hantzsch ester-initiated aryl and alkyl radical generation protocol from aryl halides (Br and Cl) and alkyl iodides. This method provides access to a wide range of benzo-fused heterocycles and C(sp3)-C(sp3) coupling products. The reductive detosylation reaction has also been demonstrated using the same reaction conditions. Initial mechanism studies provide evidence of the formation of an alkyl radical.