Cu 0 -Promoted Truce-Smiles Rearrangement for Aryl-Difluoromethylenation of C═C Bonds via a Reductive Radical-Polar Crossover Process

An efficient Cu -promoted Truce-Smiles rearrangement for the aryl-difluoromethylenation of C═C bonds by the reaction of -alkyl- -(arylsulfonyl)methacrylamide and 2-bromodifluoromethyl-1,3-benzodiazole via a reductive radical-polar crossover process under mild reaction conditions is presented. The pr...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-10, Vol.89 (19), p.13947-13952
Main Authors: Li, Hongxiao, Hu, Kaiji, Zhang, Jianhua, Jiang, Haizhen
Format: Article
Language:English
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Summary:An efficient Cu -promoted Truce-Smiles rearrangement for the aryl-difluoromethylenation of C═C bonds by the reaction of -alkyl- -(arylsulfonyl)methacrylamide and 2-bromodifluoromethyl-1,3-benzodiazole via a reductive radical-polar crossover process under mild reaction conditions is presented. The protocol enables practical access to a variety of single regioisomer α-aryl-β-difluoromethylene amides in good to excellent yields through consecutive difluoromethylenation, radical-polar crossover, 1,4-aryl migration, SO extrusion, and N-H bond formation cascade reaction.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c01074