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Rhodium/Copper-Catalyzed Annulation of Benzimides with Internal Alkynes: Indenone Synthesis through Sequential C[BOND]H and C[BOND]N Cleavage

Authors

  • Bi-Jie Li,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China)
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  • Hao-Yuan Wang,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China)
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  • Qi-Lei Zhu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China)
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  • Prof. Dr. Zhang-Jie Shi

    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 and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China)
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
    • Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing, 100871 (China)
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  • Support of this work by the “973” Project from the MOST of China (2009CB825300) and NSFC (Nos. 20925207, and 21002001) is gratefully acknowledged.

Abstract

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An zwei Stellen gebrochen: Ein Rhodium(III)-Kupfer(II)-System katalysiert die Anellierung von Benzimiden mit internen Alkinen unter Bildung von Indenonen (siehe Schema; Cp*=C5Me5). Die Reaktion umfasst die ungewöhnliche nukleophile Addition einer Übergangsmetall-Kohlenstoff-Bindung an eine Imideinheit. Dieser neuartige Prozess ermöglicht die Synthese von Indenonen aus leicht zugänglichen Ausgangsverbindungen.

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