Defluoroalkylation of Trifluoromethylarenes with Hydrazones: Rapid Access to Benzylic Difluoroarylethylamines

Abstract

Here, we report an efficient and modular approach toward the formation of difluorinated arylethylamines from simple aldehyde-derived <i>N,N</i>-dialkylhydrazones and trifluoromethylarenes (CF₃-arenes). This method relies on selective C-F bond cleavage via reduction of the CF₃-arene. We show that a diverse set of CF₃-arenes and CF₃-heteroarenes react smoothly with a range of aryl and alkyl hydrazones. The β-difluorobenzylic hydrazine product can be selectively cleaved to form the corresponding benzylic difluoroarylethylamines.