Visible-Light-Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal-Free Conditions

Authors

  • Jun Xuan,

    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    Search for more papers by this author
  • Xu-Dong Xia,

    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    Search for more papers by this author
  • Ting-Ting Zeng,

    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    Search for more papers by this author
  • Zhu-Jia Feng,

    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    Search for more papers by this author
  • Prof. Dr. Jia-Rong Chen,

    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    Search for more papers by this author
  • Dr. Liang-Qiu Lu,

    Corresponding author
    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    • CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/===

    Search for more papers by this author
  • Prof. Dr. Wen-Jing Xiao

    Corresponding author
    1. CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/
    2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (China)
    3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS (China)
    • CCNU–uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei 430079 (China) http://chem-xiao.ccnu.edu.cn/===

    Search for more papers by this author

  • We are grateful to the National Science Foundation of China (NO. 21232003, 21202053, and 21272087) and the National Basic Research Program of China (2011CB808603) for support of this research. We thank Prof. Li-Zhu Wu and Qin-Yuan Meng in Technical Institute of Physics and Chemistry (CAS) for the quantum yield measurements.

Abstract

A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful.

Ancillary