Sodium trifluoromethanesulfinate

Together with t-butyl hydroperoxide, an oxidant, this compound was found to be a suitable reagent for introducing trifluoromethyl groups onto electron-rich aromatic compounds by Langlois; this reagent is also known as the Langlois reagent.

This reaction operates via a free radical mechanism.

[1] This reagent is also able to trifluoromethylate electron-deficient aromatic compounds under biphasic conditions.

[2] Zinc difluoromethanesulfinate, a related polymeric coordination complex, is able to introduce difluoromethyl groups (CHF2-) onto aromatic compounds under similar biphasic conditions as well.

[3] With the use of DMSO as an oxidant, it provides an environmentally friendly way for the synthesis of β-trifluoromethyl alcohols from alkenes.

Structure of sodium trifluoromethylsulfinate
Structure of sodium trifluoromethylsulfinate