Bulletin of the Chemical Society of Japan · 1984 · 123 citations · 24 references
Natural SciencesChemistryBiocatalysisCatalysisOrganometallic ChemistryCatalytic MechanismsHeterocycle SynthesisAlkylation ReactionsAlkyne ActivationAlkyne Coupling ReactionsAlkyne Cycloaddition Reactions
Abstract A series of 1-alkynes (RC≡CH where R=Et, n-Pr, n-Bu, n-C6H13, cyclohexyl, Ph, Me3Si, Me3SiCH2, and Me3SiOCH2) was found to dimerize regioselectively (>99%) to 2,4-disubstituted 1-buten-3-ynes in 92–99% yields by catalysis of (η5-C5Me5)2TiCl2/i-PrMgBr at 30 °C in 1–3 h. The catalyst system is also effective for the regioselective codimerization of various 1-alkynes with 1-ethynylcyclohexene or ethynylbenzene.
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