Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles.

A method for the radical functionalization of 1,2,4‐oxadiazoles using alkyl halides as precursors of radicals is described. The reaction efficiency is determined by potassium tetrafluoropyridinyl thiolate additive, which plays dual role. First, the thiolate converts alkyl halides into more reactive fluorinated aryl sulfides, which undergo photoredox activation of the C−S bond. Second, the thiolate decreases the unproductive loss of alkyl radicals by converting them back to the sulfides. [ABSTRACT FROM AUTHOR]