Organophotoredox-Catalyzed Intermolecular Oxa-[4+2] Cycloaddition Reactions

J Org Chem. 2019 Sep 6;84(17):10669-10678. doi: 10.1021/acs.joc.9b01156. Epub 2019 Aug 1.

Abstract

An intermolecular oxa-[4+2] cycloaddition reaction promoted by a thioxanthylium photoredox catalyst under irradiation with green light has been developed. The reaction of ortho-quinone methides with styrenes smoothly affords the desired cycloadducts. Especially styrenes bearing electron-donating groups are efficiently transformed in this reaction. This method represents a sustainable way to carry out oxa-[4+2] cycloaddition reactions using only a catalytic amount of a photocatalyst and visible light.