The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(II)-Catalyzed Cycloadditions of 1-Sulfonyl 1,2,3-Triazoles with 1,3-Dienes

Authors

  • Dr. Hai Shang,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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    • These authors contributed equally to this work.

  • Yuanhao Wang,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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    • These authors contributed equally to this work.

  • Dr. Yu Tian,

    1. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100193 (China)
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  • Juan Feng,

    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
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  • Prof. Dr. Yefeng Tang

    Corresponding author
    1. The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)
    • The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084 (China)===

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  • We acknowledge the financial support from the National Science Foundation of China (21102081, 21272133), New Teachers’ Fund for Doctor Stations, Ministry of Education (20110002120011), and Beijing Natural Science Foundation (2132037).We also thank J. K. Fu of Peking University for the initiation of this work.

Abstract

The first rhodium(II)-catalyzed aza-[4+3] cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed, and enable the efficient synthesis of highly functionalized 2,5-dihydroazepines from readily available precursors. In some cases, the reaction pathway could divert to formal aza-[3+2] cycloadditions, thus leading to 2,3-dihydropyrroles. In this context, the titled reaction represents a capable tool for the divergent synthesis of two types of synthetically valuable aza-heterocycles from common rhodium(II) iminocarbene intermediates.

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