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Catalyst-Free gem-Difunctionalization of Fluoroalkyl-Substituted Diazo Compound with Diselenide or Disulfide and NFSI
Jiuling Li1, Chaoqun Ma1, Dong Xing1
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , China.
Abstract:
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.
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