Interrupted reduction of CF3SO2Cl using tricyclohexylphosphine allows for electrophilic trifluoromethylsulfinylation

Hélène Chachignon (1) , Dominique Cahard (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The monoreduction of trifluoromethanesulfonyl chloride by an appropriate phosphine, preferentially tricyclohexylphosphine, generates the reactive trifluoromethanesulfinyl chloride CF3SOCl as donor of CF3S(O)+ cation. The direct trifluoromethylsulfinylation of indoles, pyrroles, other azaarenes, amines, and phenols was successfully achieved in moderate to high yields.

Mots clés: Indole; Halogen bond; Sulfur; Fluorine; Phosphine

Domaines: Chimie

Hélène Chachignon, Dominique Cahard. Interrupted reduction of CF3SO2Cl using tricyclohexylphosphine allows for electrophilic trifluoromethylsulfinylation. Journal of Fluorine Chemistry, 2017, 198, pp.82-88. ⟨10.1016/j.jfluchem.2016.11.020⟩. ⟨hal-02046268⟩