S-Trifluoromethylated compounds are pharmaceutically interesting owing to their favorable pharmacokinetic and pharmacodynamic properties, and are also used in functional materials and agrochemicals. However, the current synthetic methods for the S-trifluoromethylation reactions involve the use of either expensive noble-metal-based organometallic catalysts, or toxic reagents. We have demonstrated a convenient visible-light photoredox catalyzed S-trifluoromethylation of various thiols under metal-free conditions, using the cost-effective sodium trifluoromethanesulfinate (Langlois regent) as the trifluoromethylating agent and diacetyl as the photocatalyst. This novel organocatalysis-based synthetic method provides a convenient and cost-effective alternative to the transition-metal-catalyzed photoredox reactions.

Metal-free photoredox-catalysis for the S-trifluoromethylation (S–CF3) of thiols

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ACS Fall 2022

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