The reaction of the phenyl-copper-magnesium reagent, prepared from 2 PhMgBr and CuI, with some organic halidesMohammed T. Rahman and Syeda K. NaharJournal of Organometallic Chemistry 329, 133-138 (1987)
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https://www.thevespiary.org/rhodium/Rhodium/chemistry/cu-grignard.coupling.html)
AbstractThe reagent prepared from 2 PhMgBr and CuI reacts with allyl and benzyl bromides to give allylbenzene and diphenylmethane, respectively, in 52 and 62% yields. The yields rise to 82-84% 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 65% yield. Iodoarenes react slowly and give poorer yields of the biaryls (18-46%); in these reactions some metal-iodine exchange is observed. 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.
