Silver-mediated radical aryltrifluoromethylthiolation of activated alkenes by S-trifluoromethyl 4-methylbenzenesulfonothioate

Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates

“…Finally, silvermediated formation of trifluoromethylthiolated oxindoles 12 was reported by Zhao and coworkers in 2018 (Scheme 5D). [24] Mechanistic studies demonstrated the necessity of the oxidant. Moreover, the reaction seems to occur through a radical pathway since no product was detected in the presence of TEMPO.…”

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

“…The reaction system was compatible with lots of functional groups, such as halogen, cyan group, acetyl, ester, and BocNH. Later in 2018, the Zhao group applied S-trifluoromethyl 4-methylbenzenesulfonothioate as SCF 3 radical precursor for the same conversion (Scheme 44) [66]. The reaction occurred in the presence of AgF and K 2 S 2 O 8 in DMSO at 20 • C. The mechanistic studies indicated that AgSCF 3 was generated from S-trifluoromethyl 4-methylbenzenesulfonothioate and AgF, and SCF 3 radicals were subsequently formed by the oxidation with K 2 S 2 O 8 .…”

Use of ArSO2SRf reagents: an efficient tool for the introduction of SRf moieties

“…22 Using II as a coupling partner and in the presence of K2S2O8, they depicted a silver mediated aryltrifluoromethylthiolation reaction of activated alkenes via a radical process. 23 Under mild conditions, the aryltrifluoromethylthiolation of a panel of activated alkenes 29 was possible with yields up to 80%. The transformation turned out to be tolerant to various functional groups such as nitro and halogens for instance.…”