Sodium trifluoromethanesulfinate
Sodium trifluoromethanesulfinate is the sodium salt of trifluoromethanesulfinic acid. 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.
This reagent is also able to trifluoromethylate electron-deficient aromatic compounds under biphasic conditions. Zinc difluoromethanesulfinate, a related polymeric coordination complex, is able to introduce difluoromethyl groups onto aromatic compounds under similar biphasic conditions as well.
With the use of DMSO as an oxidant, it provides an environmentally friendly way for the synthesis of β-trifluoromethyl alcohols from alkenes.
