Nickel-Catalyzed Methylation of Aryl Halides with Deuterated Methyl Iodide.

A nickel-catalyzed methylation of aryl halides with cheap and readily available CH3 I or CD3 I is described. The reaction is applicable to a wide range of substrates and allows installation of a CD3 group under mild reaction conditions without deuterium scrambling to other carbon atoms. Initial mechanistic studies on the stoichiometric and catalytic reactions of the isolated [(dppp)Ni(C6 H4 -4-CO2 Et)Br] [dppp=1,3-bis(diphenylphosphanyl)propane] suggest that a Ni(0) /Ni(II) catalytic cycle is favored.