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Reductive Cleavage of the Cmath image[BOND]Cmath image Bond of Secondary Benzyl Alcohols: Rhodium Catalysis Directed by N-Containing Groups

Authors

  • Kang Chen,

    1. Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
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  • Hu Li,

    1. Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
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  • Zhi-Quan Lei,

    1. Chengdu Institute of Biology, Chinese Academy of Science, Chengdu, Sichuan 610068 (China)
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  • Yang Li,

    1. Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
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  • Wen-He Ye,

    1. Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
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  • Li-Sheng Zhang,

    1. Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
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  • Prof. Jian Sun,

    1. Chengdu Institute of Biology, Chinese Academy of Science, Chengdu, Sichuan 610068 (China)
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  • Prof. Dr. Zhang-Jie Shi

    Corresponding author
    1. Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Science, Shanghai 200032 (China)
    • Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (China)
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  • Support of this work by the “973” Project from the MOST of China (2009CB825300) and NSFC (Nos. 20925207 and 21002001) is gratefully acknowledged.

Abstract

original image

Cutting loose: 1,1-Biarylmethanol substrates undergo reductive cleavage of the C[BOND]C bond in the presence of a cationic RhIII catalyst and H2 (see scheme; DG=directing group). Various functional groups are tolerated in the reaction system. Preliminary studies indicate that a five-membered rhodacycle intermediate, which then converts into a RhIII hydride species for the reduction, is involved in the catalytic cycle.

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