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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| Published in | Journal of the American Chemical Society Vol. 136; no. 16; pp. 5920 - 5922 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
23.04.2014
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Geary, Laina M Chen, Te-Yu Montgomery, T. Patrick Krische, Michael J |
| AuthorAffiliation | Department of Chemistry and Biochemistry University of Texas at Austin |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24724733$$D View this record in MEDLINE/PubMed |
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| Keywords | DEOXYDEHYDRATION LARGER ACENES COMPLEXES CHEMISTRY HETEROACENES HYDROXYCARBONYL FISSION |
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| Snippet | A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol–diene [4+2]... A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2]... |
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| SubjectTerms | Catalysis Chemistry Chemistry, Multidisciplinary Cycloaddition Reaction Fluorenes - chemical synthesis Fluorenes - chemistry Physical Sciences polycyclic aromatic hydrocarbons ruthenium Ruthenium - chemistry Science & Technology standard operating procedures |
| Title | Benzannulation via Ruthenium-Catalyzed Diol–Diene [4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes and Acenes |
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