Iron-phosphine, -phosphite, -arsine and –carbene catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents

Bedford, Robin B., Betham, Michael, Bruce, Duncan W., Danopoulos, Andreas A., Frost, Robert M. and Hird, Michael (2006) Iron-phosphine, -phosphite, -arsine and –carbene catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents. Journal of Organic Chemistry, 71 (3), 1104-1110. (doi:10.1021/jo052250+).

Abstract

Simple catalysts formed in situ from iron chloride and a wide range of monodentate and bidentate phosphines and arsines have been screened in the coupling of alkyl halides bearing â-hydrogens with aryl Grignard reagents. The best of these show excellent activity, as do catalysts formed in situ with monodentate trialkyl and triaryl phosphite ligands. N-heterocyclic carbene-based precatalysts, either preformed or made in situ, also show excellent performance.

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