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Catalyst-Free Intramolecular Formal Carbon Insertion into σ-C[BOND]C Bonds: A New Approach toward Phenanthrols and Naphthols

Authors

  • Ying Xia,

    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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  • Peiyuan Qu,

    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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  • Zhenxing Liu,

    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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  • Rui Ge,

    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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  • 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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  • 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. 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)
    • 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), NSFC (Grant No. 21272010, 20832002).

Abstract

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Die unterschiedliche Reaktivität der zwei verschiedenen Carbonylgruppen in Substraten mit Keton- und Aldehyd-Funktionalität wurde für die Synthese von Phenanthrolen, Naphtholen und ihren Heteroatom-Analoga genutzt. Schlüssel dieser hocheffizienten und robusten Methode ist die katalysatorfreie intramolekulare formale Insertion des Diazo-Kohlenstoffatoms von N-Tosylhydrazonen in die C-C-Bindung von Ketonen (siehe Schema).

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