Vinyl fluoromethyl thioethers are widely employed as pivotal intermediates in organic synthesis and deemed as promising scaffolds in drug candidates. Herein, we report a general and concise strategy for the stereoselective fluoromethylthiolation of enamides, enabling the modular assembly of vinyl di-/trifluoromethyl thioethers from bench-stable fluoromethylthiolating reagents. This mild protocol exhibits broad functional group compatibility, as demonstrated by over 40 examples, including enamides derived from bio-active moleculars. Furthermore, the utility of this method is highlighted through the late-stage modification of the approved probenecid drug and a series of synthetic applications. Mechanistic investigations, including control experiments, Stern–Volmer quenching, and light on–off experiments, elucidate the photoredox radical reaction pathway.

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