Trifluoromethylation Reactions with Potassium Trifluoromethanesulfinate under Electrochemical Oxidation

Abstract

The electrochemical oxidation of potassium trifluoromethanesulfinate (CF 3 SO 2 K) in the presence of electron-rich aromatics and alkenes provides the corresponding trifluoromethylated products.

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…Tommasino and co-workers have used potassium trifluoromethylsulfinate to effect electrochemical trifluoromethylation of dimethoxybenzenes, durene, and several olefins. 83 …”

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

“…Potassium trifluoromethanesulfinate was used as a source of CF 3 obtained by electrochemical oxidation; in this way, electron rich alkenes provided mixtures of the corresponding saturated and unsaturated (major) products (Scheme 51-a) [151]. Alkenes were also reacted under photochemical activation with trifluoromethanethiosulfonates CF 3 SO 2 SR, or trifluorothioacetates CF 3 COSR in up to 50% yield (Scheme 51-b) [152].…”

Addition of CF3 across unsaturated moieties: a powerful functionalization tool

“…15 Later, the hydrotrifluoromethylation of α,β-unsaturated ketones in the presence of RhCl(PPh 3 ) 3 and Et 2 Zn was reported. In this reaction, CF 3 I was employed as a trifluoromethyl source and α-trifluoromethylated carbonyl compounds were obtained in moderate yields.…”