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Tandem Hydroformylation–Hydrogenation of 1-Decene Catalyzed by Rh-Bidentate Bis(trialkylphosphine)s

Authors

  • Takeo Ichihara,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan), Fax: (+81) 3-5841-7263
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  • Koji Nakano Dr.,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan), Fax: (+81) 3-5841-7263
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  • Masaya Katayama,

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan), Fax: (+81) 3-5841-7263
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  • Kyoko Nozaki Prof. Dr.

    1. Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan), Fax: (+81) 3-5841-7263
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Abstract

A series of 2,2′-bis[(dialkylphosphino)methyl]biphenyls (alkyl-BISBIs) were synthesized and applied to the tandem hydroformylation–hydrogenation of 1-decene. The alkyl-BISBI ligands with “small” primary alkyl groups such as methyl or n-hexyl groups on the phosphorus atoms provided 1-alkanols selectively, whereas those with larger alkyl groups such as isopropyl or neopentyl groups showed much lower conversion from alkanals to alkanols. Observation of rhodium complexes of the BISBI-type ligands under H2/CO atmosphere revealed that the presence of a stable [RhH(CO)2(ligand)] species seems to be less favorable for the second step, the hydrogenation of aldehydes.

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