Trifluoromethylations trifluoromethyl diphenylsulfonium triflate

Kinetic Parameters for the Trifluoromethylation of Aniline with 5-(Trifluoromethyl)dibenzothiophenium Triflate (17), S-(Trifluoromethyl)diphenylsulfonium Triflate (29), AND 5-(Trifluoromethyl)-3,7-DINITRODIBENZOTHIOPHENIUM TrIFLATE (39) IN DMF-d7 AT 25°C... 

Trifluoromethyl)diphenylsulfonium triflate can be reduced by Cu metal, converting iodo-substituted aromatics and heteroaromatics into the corresponding trifluoromethylated compounds in high yield (eq 1). ... 

The reaction of (5)-(trifluoromethyl)diphenylsulfonium triflate with Na2S204 or H0CH2S02Na under suitable conditions can generate the CF3 radical without further reduction. Various styrenes react with (5)-(trifluoromethyl)diphenylsulfonium triflate in the presence of H0CH2S02Na-2H20 or Na2S204, furnishing a-trifluoromethylated ketones (eq 4). ... 

In a recent paper, 5-(trifluoromethyl)diphenylsulfonium triflate (545) in the presence of copper was proposed as an efficient reagent for trifluoromethylation of heteroaromatic compounds [282]. In particular, 3-chloro-6-iodopyridazine smoothly reacted with this reagent to give the product of the iodine selective substitution (546) in 98 % yield (Scheme 109). The proposed mechanism for the formation of active species included reduction of 545 leading to trifluoromethyl radicals, which in turn reacted with copper to give CFjCu. 

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