A New Reagent for Direct Difluoromethylation
Journal of the American Chemical Society2012Vol. 134(3), pp. 1494–1497
Citations Over TimeTop 1% of 2012 papers
Yuta Fujiwara, Janice A. Dixon, Rodrigo A. Rodriguez, Ryan D. Baxter, Darryl D. Dixon, Michael R. Collins, Donna G. Blackmond, Phil S. Baran
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.
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