Synthesis of α-Aryl Esters and Nitriles: Deaminative Coupling of α-Aminoesters and α-Aminoacetonitriles with Arylboronic Acids

Authors

  • Guojiao Wu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) 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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  • Yifan Deng,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) 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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    • These authors contributed equally to this work.

  • Chaoqiang Wu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) 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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    • These authors contributed equally to this work.

  • Dr. Yan Zhang,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) 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. Jianbo Wang

    Corresponding author
    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China)
    2. The State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
    • Beijing National Laboratory of Molecular Sciences (BNLMS) 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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  • The project is supported by the 973 Program (No. 2012CB821600) and NSFC (Grant Nos. 21272010 and 21332002).

Abstract

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)[BOND]N bonds into C(sp3)[BOND]C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up.

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