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Synergistic Catalysis in the Sonogashira Coupling Reaction: Quantitative Kinetic Investigation of Transmetalation

Authors

  • Chuan He,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (P.R. China)
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  • Jie Ke,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (P.R. China)
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  • Huan Xu,

    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (P.R. China)
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  • Prof. Aiwen Lei

    Corresponding author
    1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (P.R. China)
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032 (P.R. China)
    • College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (P.R. China)
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  • This work was supported by the “973” Project from the MOST of China (2011CB808600) and the National Natural Science Foundation of China (21025206, 20832003, 20972118, 20972119). We also thank “the Fundamental Research Funds for the Central Universities”, Program for New Century Excellent Talents in University (NCET) and the Program for Changjiang Scholars and Innovative Research Team in University (IRT1030).

Abstract

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Rate-limiting: The transmetalation step of the Sonogashira coupling reaction has been established as the rate-limiting step. This cross-coupling has been demonstrated to be a Pd-catalyzed and Cu-catalyzed synergistic process, which exhibits a first-order kinetic dependence on both the [Pd] and [Cu] catalysts (see scheme).

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