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Palladium-Catalyzed C(sp3)[BOND]H Activation: A Facile Method for the Synthesis of 3,4-Dihydroquinolinone Derivatives

Authors

  • Jia-Xuan Yan,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)
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  • Dr. Hu Li,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)
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  • Dr. Xiang-Wei Liu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)
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  • Jiang-Ling Shi,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)
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  • Xin Wang,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)
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  • Prof. Dr. Zhang-Jie Shi

    Corresponding author
    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
    • Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871 (China)===

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  • Support from the NSFC (J1030413, 20925207, and 20821062) and the “973” Project from the MOST of China (2009CB825300) is gratefully acknowledged.

Abstract

3,4-Dihydroquinolinones were synthesized by the palladium-catalyzed, oxidative-addition-initiated activation and arylation of inert C(sp3)[BOND]H bonds. Pd(OAc)2 and P(o-tol)3 were used as the catalyst and ligand, respectively, to improve the efficiency of the reaction. A further advantage of this reaction is that it could be performed in air. A relatively rare seven-membered palladacycle was proposed as a key intermediate of the catalytic cycle.

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