Abstract
The stoichiometry and the kinetics of tho reaction between various Grignard reagents and alkyl halides with a copper catalyst have been examined in tetrahydrofuran solutions. The catalytically active species is an organocopper(I) complex produced by the rapid motathesis between copper(I) and -(II) halides and Grignard reagents. Primary alkyl bromides react with various Grignard reagents under these conditions to produce cross-coupled dimers exclusively. A mechanism is proposed in which coupling occurs between the alkyl halide and the alkylcopper(I) intermediate by displacement of the halide. On the other hand, only disproportionation products are produced from secondary and tertiary alkyl halides due to the unfavorable displacement process. The rate and the mechanism of the thermal decomposition of alkylcopper(I) species under the reaction conditions as well as sidereactions involved in the coupling reaction are described.
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