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A new reagent for direct difluoromethylation.

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 ?-systems and thiols. Regiochemical comparisons suggest that the CF(2)H radical generated from the new reagent possesses nucleophilic character.

SUBMITTER: Fujiwara Y

PROVIDER: S-EPMC3269891 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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A new reagent for direct difluoromethylation.

Fujiwara Yuta Y Dixon Janice A JA Rodriguez Rodrigo A RA Baxter Ryan D RD Dixon Darryl D DD Collins Michael R MR Blackmond Donna G DG Baran Phil S PS

Journal of the American Chemical Society 20120113 3

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 cl ...[more]

PMID: 22229949

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