Journal of the American Chemical Society 2012-01-25

A new reagent for direct difluoromethylation.

Yuta Fujiwara, Janice A Dixon, Rodrigo A Rodriguez, Ryan D Baxter, Darryl D Dixon, Michael R Collins, Donna G Blackmond, Phil S Baran

Index: J. Am. Chem. Soc. 134 , 1494-1497, (2012)

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Abstract

Molecular scaffolds containing alkylfluorine substituents are desired in many areas of chemical research from materials to pharmaceuticals. Herein, we report the invention of a new reagent (Zn(SO(2)CF(2)H)(2), DFMS) for the innate difluoromethylation of organic substrates via a radical process. This mild, operationally simple, chemoselective, and scalable difluoromethylation method is compatible with a range of nitrogen-containing heteroarene substrates of varying complexity as well as select classes of conjugated π-systems and thiols. Regiochemical comparisons suggest that the CF(2)H radical generated from the new reagent possesses nucleophilic character.© 2012 American Chemical Society