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

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

The different reactivity of two kinds of carbonyl groups in keto aldehyde substrates has been exploited for the synthesis of phenanthrols, naphthols, and their heteroatom‐containing analogues. Key to this highly efficient and robust methodology is the catalyst‐free intramolecular formal diazo carbon...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-02, Vol.52 (9), p.2543-2546
Hauptverfasser: Xia, Ying, Qu, Peiyuan, Liu, Zhenxing, Ge, Rui, Xiao, Qing, Zhang, Yan, Wang, Jianbo
Format: Artikel
Sprache:eng
Schlagworte:
1,2‐shift
2-shift
Aldehydes
Carbon
Carbonyl groups
Catalysts
cyclization
diazo compounds
hydrocarbons
Insertion
Methodology
Naphthol
Synthesis
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Beschreibung
Zusammenfassung:The different reactivity of two kinds of carbonyl groups in keto aldehyde substrates has been exploited for the synthesis of phenanthrols, naphthols, and their heteroatom‐containing analogues. Key to this highly efficient and robust methodology is the catalyst‐free intramolecular formal diazo carbon insertion of N‐tosylhydrazones into keto CC bonds (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201209269