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Palladium-Catalyzed Three-Component Reaction of Allenes, Aryl Iodides, and Diazo Compounds: Approach to 1,3-Dienes

Authors

  • Qing Xiao,

    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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  • Binglong Wang,

    1. College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021 (China)
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  • Leiming Tian,

    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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  • Yang Yang,

    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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  • Jian Ma,

    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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  • 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. Shufeng Chen,

    Corresponding author
    1. College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021 (China)
    • Shufeng Chen, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021 (China)

      Jianbo Wang, 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)
    • Shufeng Chen, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021 (China)

      Jianbo Wang, 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 National Basic Research Program of China (973 Program, No. 2009CB825300), Natural Science Foundation of China (Grant No. 21272010, 21262023), and the Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (NJYT-12-B03).

Abstract

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'Diene' to know: The title reaction leads to the formation of 1,3-dienes in high yields (see scheme). The reaction also proceeds with the use of N-tosylhydrazone substrates. Carbopalladation to the allene and palladium carbene migratory insertion are proposed to play the key role in this transformation.

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