Photocatalyzed Decarboxylative Thiolation of Carboxylic Acids Enabled by Fluorinated Disulfide

Thiolation of carboxylic acids using a disulfide reagent having tetrafluoropyridinyl groups is described. The light-mediated process is performed using an acridine-type photocatalyst. Primary, secondary, tertiary, and heteroatom-substituted carboxylic acids can be thiolated, and the method can be applied to the late-stage modification of a range of naturally occurring compounds and drugs. The fluorinated pyridine fragment is believed to enable the C-S bond formation. The resulting sulfides were used as redox-active radical precursors.

Automated summary

This study describes the thiolation of carboxylic acids using a disulfide reagent with tetrafluoropyridinyl groups, which is mediated by light and an acridine-type photocatalyst. The method can be applied to various types of carboxylic acids and is useful for the late-stage modification of natural compounds and drugs. The formation of C-S bond is believed to be facilitated by the presence of the fluorinated pyridine fragment. The resulting sulfides can serve as redox-active radical precursors.