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Suzuki–Miyaura Coupling Reaction by PdII-Catalyzed Aromatic C[BOND]H Bond Activation Directed by an N-Alkyl Acetamino Group

Authors

  • Zhangjie Shi Dr.,

    1. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Fax: (+86) 10-6276-0890 http://www.shigroup.cn/
    2. 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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  • Bijie 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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  • Xiaobing Wan Dr.,

    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 Cheng Prof. Dr.,

    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. College of Chemistry and Material Sciences, Wenzhou University, Wenzhou, Zhejiang 325027, China
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  • Zhao Fang,

    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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  • Bin Cao,

    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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  • Changming Qin,

    1. College of Chemistry and Material Sciences, Wenzhou University, Wenzhou, Zhejiang 325027, China
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  • Yang 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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Errata

This article is corrected by:

  1. Errata: Suzuki–Miyaura Coupling Reaction by PdII-Catalyzed Aromatic C[BOND]H Bond Activation Directed by an N-Alkyl Acetamino Group Volume 46, Issue 41, 7730, Article first published online: 4 October 2007

  • Support of this work by a starter grant from Peking University and the grant from the National Sciences of Foundation of China (No. 20542001, 20521202, 20672006) is gratefully acknowledged. We thank Professor Qinghua Fan at ICCAS for compounds 1 c, 1 d, and 1 e.

Abstract

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A seamless join: An efficient method to construct a C(sp2)[BOND]C(sp2) bond has been developed by using a Suzuki–Miyaura-type coupling of N-alkyl acetanilides with boronic acids. The reaction was catalyzed by a PdII species and the C[BOND]H bond activation was directed by the acetamino group (see scheme). This reaction offers a halogen-free method to construct complicated structures.

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