4- 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... 

PDI value could be obtained with high conversion. It is understood that the mechanism of the reaction proceeds through an electron transfer between the excited diaryliodonium salt and the nitroxide during the propagation process [YOS 10a]. Similarly, the use of a triarylsulfonium salt, namely (4-tert-butylphenyl)-diphenylsulfonium triflate, as the photoacid generator in the same process for controlled photoinduced NMRP of MMA has also been reported [YOS 10b]. However, the mechanism still has unclear points as the function of the iodonium salt is unknown. 

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. 

The Michael addition of a- or / -substituted ketones (545) (X=0, NTs, NNs n = 1 or 2) to CF3-substituted vinyl diphenylsulfonium triflate (546) has been developed as an annulation reaction, which affords the a-CF3 substituted, epoxide-fused heterocycles (547) (pyrrolidines, piperidines, and tetrahydrofurans) with >20 1... 

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