The reaction of phenyl-copper-magnesium reagent, prepared from 2 PhMgBr and CuI, with some organic halides

Article abstract of DOI:10.1016/S0022-328X(00)98901-0

The reagent prepared from 2 PhMgBr and CuI reacts with allyl and benzyl bromides to give allylbenzene and diphenylmethane, respectively, in 52 and 62percent yields.The yields rise to 82-84percent in the presence of nitrobenzene as an oxidant.During the reaction with allyl bromide some copper-bromine exchange takes place.Methyl iodide reacts with the copper reagent to give toluene in 65percent yield.Iodoarenes react slowly and give poorer yields of the biaryls (18-46percent); in these reactions some metal-iodine exchange is obvserved.Nitrobenzene seems to be better as an oxidant than copper(II) chloride, which brings about some metal-chlorine exchange in addition to acting as an oxidant.