Benzannulation via Ruthenium-Catalyzed Diol–Diene [4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes and Acenes

A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol–diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 136; no. 16; pp. 5920 - 5922
Main Authors Geary, Laina M, Chen, Te-Yu, Montgomery, T. Patrick, Krische, Michael J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.04.2014
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cycloaddition Reaction
Fluorenes - chemical synthesis
Fluorenes - chemistry
Physical Sciences
polycyclic aromatic hydrocarbons
ruthenium
Ruthenium - chemistry
Science & Technology
standard operating procedures
DEOXYDEHYDRATION
LARGER ACENES
COMPLEXES
CHEMISTRY
HETEROACENES
HYDROXYCARBONYL
FISSION
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Summary:A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol–diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja502659t