A New Reagent for Direct Difluoromethylation

作者：Fujiwara, Yuta; Dixon, Janice A.; Rodriguez, Rodrigo A.; Baxter, Ryan D.; Dixon, Darryl D.; Collins, Michael R.; Blackmond, Donna G.; Baran, Phil S.^*

来源：Journal of the American Chemical Society, 2012, 134(3): 1494-1497.

DOI：10.1021/ja211422g

• BIOLOGICAL EVALUATION
• HETEROAROMATIC BASES
• PRACTICAL SYNTHESIS
• SUBSTITUTIONS
• HETEROCYCLES
• INHIBITORS
• ANALOGS

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(SO2CF2H)(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 pi-systems and thiols. Regiochemical comparisons suggest that the CF2H radical generated from the new reagent possesses nucleophilic character.

• 出版日期2012-1-25