Organic Letters · 2004 · 85 citations · 21 references
Natural SciencesChemistryCatalysisOrganic ChemistryCatalytic MechanismsCross-coupling ReactionsReaction MechanismsAlkenyl Halide CouplingAlkyl Cross-couplingAlkylation ReactionsCross CouplingCross-coupling CatalysisKumada CouplingReaction CouplingReductive Cross-coupling
[reaction: see text] Pd(2)(dba)(3)-Ph(3)P-catalyzed Kumada-Corriu coupling reactions of unactivated alkyl bromides or iodides with an alkynyl nucleophile furnish C(sp)-C(sp)3 bond formation. Alkynyl nucleophiles can be alkynyllithiums or the corresponding Grignard reagents. The superior performance of Ph(3)P ligand over the trialkylphosphine ligands indicates that this cross-coupling reaction may be a reductive-elimination-controlled process.
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Jan H. Kirchhoff, Matthew R. Netherton, Ivory D. Hills et al. · Journal of the American Chemical Society · 2002 · 357 citations