title: PhI(OAc)(2) -mediated radical trifluoromethylation of vinyl azides with Me(3)SiCF(3).
abstract: The fluorine-containing organic motif is becoming privileged in pharmaceuticals, agrochemicals, and functional materials, owing to its unique properties such as electron-withdrawing character, metabolic stability, and lipophilicity. Described herein is the PhI(OAc)2 -mediated radical trifluoromethylation of vinyl azides with Me3 SiCF3 to efficiently generate α-trifluoromethyl azines. The resulting α-trifluoromethyl azines were successfully transformed to valuable fluorine-containing molecules such as α-trifluoromethyl ketones, β-trifluoromethyl amines, 5-fluoropyrazoles, and trifluoroethyl isoquinolines.
authors: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors: Yi-Feng
authors: YF
authors: Wang
authors: Geoffroy Hervé
authors: GH
authors: Lonca
authors: Shunsuke
authors: S
authors: Chiba
mesh_terms: D000085:Acetates / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*
chemical_list: D000085:Acetates; D001386:Azides; D005609:Free Radicals; D006845:Hydrocarbons, Fluorinated; D007462:Iodobenzenes; D017646:Organosilicon Compounds; C000591320:alpha-trifluoromethyl azine; C008857:phenyliodosodiacetate
keywords: fluorine; heterocycles; hypervalent iodine; radicals; synthetic methods