Photoredox-Mediated, Nickel-Catalyzed Trifluoromethylthiolation of Aryl and Heteroaryl Iodides

ABSTRACT: While trifluoromethylthiolation of aryl halides has been extensively explored, the current methods require complex and/or air-sensitive catalysts. Reported here is a method employing a bench-stable Ni(II) salt and an iridium photocatalyst that can mediate the trifluoromethylthiolation of a wide range of electronically diverse aryl and heteroaryl iodides, likely via a Ni(I)/Ni(III) catalytic cycle. The reaction has broad functional group tolerance and potential for application in medicinal chemistry, as demonstrated by a late-stage functionalization approach to access (racemic)-Monepantel.

Automated summary

This study presents a method using a stable Ni(II) salt and an iridium photocatalyst for the trifluoromethylthiolation of diverse aryl and heteroaryl iodides. The reaction demonstrates broad functional group tolerance and potential application in medicinal chemistry.