Zinc TrifluoroMethanesulfinate

Zinc trifluoromethanesulfinate (TFMS) is part of a zinc sulfinate toolbox developed by Phil Baran for the simple and rapid diversification of heterocycles.

Practical and Innate Carbon-Hydrogen Functionalization of Heterocycles

Learn More at the Professor and Product Portal of Professor Phil S. Baran.

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation

A preparative method of Zinc TrifluoroMethanesulfinate (TFMS): The addition of trifluoromethanesulfonyl chloride to excess Zn dust in H2O at 0 °C. After warming slowly to room temperature over 3 h, the excess Zn is removed via filtration through a pad of sand on a sintered glass funnel and washed with MeOH. The filtrate is then concentrated in vacuo at 40 °C, which is then dried further with the addition of toluene to remove H2O as an azeotropic mixture, resulting in an off-white powder. All of the ZnCl2 impurities can be removed by performing a 1:1 EtOAc:CH2Cl2 wash because ZnCl2 dissolves in 1:1 EtOAc:CH2Cl2, but TFMS does not dissolve as well. The obtained solid is dried under high vacuum for a few hours before use.