Many reagents have been developed for the trifluoromethylation of arenes and heteroarenes. While these reagents and their associated methodologies are quite effective, there remains to be a cost-effective means for trifluoromethylation on preparative scale. Trifluoroacetic acid and its anhydride represent the ideal in terms of cost and availability as sources of CF<sub>3</sub>, and present signficant opportunity for a scalable trifluoromethylation methdology; however, the decarboxylation of TFA has been shown to require high temperatures, stoichiometric metal promoters, or strongly oxidizing conditions. We report a general method for the decarboxylation of TFAA using photocatalysis and a sacrificial redox auxiliary, which allows for the trifluoromethylation of a variety of arenes under mild electrochemical potentials. This chemistry has been applied on up to 100 gram scale in batch, demonstrating its efficacy as a scalable methodology.

Trifluoroacetic anhydride as a reagent for trifluoromethylation

250th National Meeting (2015)

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