A new reagent for direct difluoromethylation.
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.
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Yuta
Y
Fujiwara
Janice A
JA
Dixon
Rodrigo A
RA
Rodriguez
Ryan D
RD
Baxter
Darryl D
DD
Dixon
Michael R
MR
Collins
Donna G
DG
Blackmond
Phil S
PS
Baran
D017611:Fluorine Compounds / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D008745:Methylation; D008958:Models, Molecular; D015032:Zinc / Q000737:chemistry
D017611:Fluorine Compounds; D007202:Indicators and Reagents; D015032:Zinc