Catalyst-Free gem-Difunctionalization of Fluoroalkyl-Substituted Diazo Compound with Diselenide or Disulfide and NFSI.

The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.