A New Reagent for Direct Difluoromethylation

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• 作者：Yuta Fujiwara ; Janice A. Dixon ; Rodrigo A. Rodriguez ; Ryan D. Baxter ; Darryl D. Dixon ; Michael R. Collins ; Donna G. Blackmond ; Phil S. Baran
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：January 25, 2012
• 年：2012
• 卷：134
• 期：3
• 页码：1494-1497
• 全文大小：380K
• 年卷期：v.134,no.3(January 25, 2012)
• ISSN：1520-5126

文摘

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 蟺-systems and thiols. Regiochemical comparisons suggest that the CF₂H radical generated from the new reagent possesses nucleophilic character.