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Nickel‐Catalyzed Methylation of Aryl Halides with Deuterated Methyl Iodide
Author(s) -
Hu Lu,
Liu Xin,
Liao Xuebin
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604406
Subject(s) - catalysis , aryl , chemistry , methyl iodide , nickel , halide , propane , stoichiometry , iodide , deuterium , catalytic cycle , medicinal chemistry , photochemistry , inorganic chemistry , organic chemistry , alkyl , quantum mechanics , physics
A nickel‐catalyzed methylation of aryl halides with cheap and readily available CH 3 I or CD 3 I is described. The reaction is applicable to a wide range of substrates and allows installation of a CD 3 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(C 6 H 4 ‐4‐CO 2 Et)Br] [dppp=1,3‐bis(diphenylphosphanyl)propane] suggest that a Ni 0 /Ni II catalytic cycle is favored.