A large number of reagents have been developed for the synthesis of trifluoromethylated compounds. However, an ongoing challenge in trifluoromethylation reaction is the use of less expensive and practical trifluoromethyl sources. We report herein the unprecedented direct trifluoromethylation of (hetero)arenes using trifluoromethanesulfonic anhydride as a radical trifluoromethylation reagent by merging photoredox catalysis and pyridine activation. Furthermore, both of the CF3 and OTf groups of trifluoromethanesulfonic anhydride were introduced into internal alkynes to access tetrasubstituted trifluoromethylated alkenes. In addition, a scalable and operationally simple decarboxylative trifluoromethylation of (hetero)arenes with easily accessible C6F5I(OCOCF3)2 under photoredox catalysis was developed. This method was tolerant of various (hetero)arenes and functional groups. Notably, C6F5I was recycled from the decarboxylation reaction and further used for the preparation of C6F5I(OCOCF3)2.

Low-cost and versatile trifluoromethylation reagents

256th National Meeting (2018)

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