Elements of Regiocontrol in the Direct Heteroarylation of Indoles/Pyrroles: Synthesis of Bi- and Fused Polycyclic Heteroarenes by Twofold or Tandem Fourfold C[BOND]H Activation

Authors

  • Dr. Zhen Wang,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Dr. Feijie Song,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Yinsong Zhao,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Yumin Huang,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Lei Yang,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Dr. Dongbing Zhao,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Prof. Dr. Jingbo Lan,

    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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  • Prof. Dr. Jingsong You

    Corresponding author
    1. Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
    • Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064 (P.R. China), Fax: (+86) 28-85412203
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Abstract

original image

Cross-coupling: The “chelation-directed control” and “catalytic-system-based control” strategies effectively switch the C2/C3-site selectivity in the heteroarylation of indoles and pyrroles with N-heteroarenes by a palladium-catalyzed twofold C[BOND]H activation to form biheteroarenes and are further extended to the synthesis of complex fused tri- and tetracyclic heteroarenes by a tandem fourfold C[BOND]H activation (see scheme).

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