Visible-Light-Induced Reductive Coupling of Arylacetylenes with Benzothiazole Sulfones

J Org Chem. 2023 Sep 1;88(17):12776-12782. doi: 10.1021/acs.joc.3c01554. Epub 2023 Aug 23.

Abstract

In this study, we propose heavy-metal-free reductive coupling of arylacetylenes with benzothiazole sulfones. The reactions of alkyl or benzylic benzothiazole sulfones with arylacetylenes are successfully performed in the presence of Hantzsch esters and K2CO3 under visible-light irradiation to afford 1,2-disubstituted alkenes in moderate to good yields, with Z-isomer as the major product. The utility of this protocol is expanded to α-deuterative coupling using a deuterated Hantzsch ester, furnishing the corresponding alkenes with high deuterium incorporation.