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Copper-Catalyzed Highly Selective Semihydrogenation of Non-Polar Carbon-Carbon Multiple Bonds using a Silane and an Alcohol

Authors

  • Kazuhiko Semba,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Fax: (+81)-75-383-2514; phone: (+81)-75-383-2515
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  • Tetsuaki Fujihara,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Fax: (+81)-75-383-2514; phone: (+81)-75-383-2515
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  • Tinghua Xu,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Fax: (+81)-75-383-2514; phone: (+81)-75-383-2515
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  • Jun Terao,

    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Fax: (+81)-75-383-2514; phone: (+81)-75-383-2515
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  • Yasushi Tsuji

    Corresponding author
    1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Fax: (+81)-75-383-2514; phone: (+81)-75-383-2515
    • Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, Fax: (+81)-75-383-2514; phone: (+81)-75-383-2515
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Abstract

A copper catalyst bearing a suitable Xantphos derivative or NHC ligand was found to be highly efficient for the selective semihydrogenation of non-polar unsaturated compounds using a mixture of a silane and an alcohol as reducing agent. The catalytic system was useful for the selective semihydrogenation of internal alkynes to (Z)-alkenes with suppression of overreduction to the corresponding alkanes. Furthermore, semihydrogenations of terminal alkyne, 1,2-diene, 1,3-diene, 1,3-enyne and 1,3-diyne systems were also achieved selectively.

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