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Highly Selective Metal Catalysts for Intermolecular Carbenoid Insertion into Primary C[BOND]H Bonds and Enantioselective C[BOND]C Bond Formation

Authors

  • Hung-Yat Thu Dr.,

    1. Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road (Hong Kong), Fax: (+852) 2857-1586
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  • Glenna So-Ming Tong Dr.,

    1. Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road (Hong Kong), Fax: (+852) 2857-1586
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  • Jie-Sheng Huang Dr.,

    1. Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road (Hong Kong), Fax: (+852) 2857-1586
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  • Sharon Lai-Fung Chan Dr.,

    1. Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road (Hong Kong), Fax: (+852) 2857-1586
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  • Qing-Hai Deng,

    1. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 354 Feng Lin Road, Shanghai 200032 (China)
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  • Chi-Ming Che Prof. Dr.

    1. Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road (Hong Kong), Fax: (+852) 2857-1586
    2. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 354 Feng Lin Road, Shanghai 200032 (China)
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  • This work was supported by The University of Hong Kong (University Development Fund), the University Grants Council of HKSAR (the Area of Excellence Scheme: AoE 10/01P), and the Hong Kong Research Grants Council (HKU 7012/05P). We thank Dr. Nianyong Zhu for solving the crystal structure of [Rh(N-CH2CO2Et-ttp)(Me)]ClO4 and Dr. Herman H. Y. Sung (The Hong Kong University of Science and Technology) for collecting the X-ray diffraction data of catalyst III. Q.-H.D. is gratefully to the Croucher Foundation of Hong Kong for a postgraduate studentship.

Abstract

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Primäre C-H-Aktivierung! Der Rhodiumkomplex I eines Doppeltaschenporphyrins katalysiert die Carbenoidinsertion in die C-H-Bindungen von n-Alkanen mit primär/sekundär-Selektivitäten bis 11.4:1 (pro C-H-Bindung, siehe Bild). Die Funktionalisierung sekundärer C-H-Bindungen mit einem Rhodiumkomplex von Haltermans chiralem Porphyrin als Katalysator ergab maximal 93 % ee. Bei diesen Reaktionen wurden auch nach fünffacher Katalysatorrückgewinnung noch Umsatzzahlen von 6477 erreicht.

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