title: Direct transformation of methyl imines to α-iminonitriles under mild and transition-metal-free conditions.
abstract: A novel transformation of methyl imines into α-iminonitriles under mild and transition-metal-free conditions is described. Three C sp 3-H bonds are cleaved in a radical pathway at room temperature under air. Simple bromide salts are employed to assist this radical process (see scheme; FG=functional group, PIDA = iodobenzene diacetate, TMS = trimethylsilyl).
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, PR China.
authors.forename: Feng
authors.initials: F
authors.lastname: Chen
authors.forename: Xiaoqiang
authors.initials: X
authors.lastname: Huang
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Cui
authors.forename: Ning
authors.initials: N
authors.lastname: Jiao
mesh_terms: D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D005609:Free Radicals / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D028561:Transition Elements / Q000737:chemistry
chemical_list: D005609:Free Radicals; D007097:Imines; D009570:Nitriles; D028561:Transition Elements; D002244:Carbon; D006859:Hydrogen
keywords: CH activation; nitriles; radical reactions; rearrangement; transition-metal free