| Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway. | |
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MedLine Citation:
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PMID: 18357988 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The first example of the palladium-catalyzed exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls has been demonstrated. In contrast to the reported earlier carbocyclizations proceeding via the Friedel-Crafts mechanism, this hydroarylation efficiently proceeds with electron-neutral and electron-deficient arenes, producing fluorene frameworks with defined stereochemistry of the double bond. On the basis of the high reactivity of electron-deficient arenes toward cyclization, high values of inter- and intramolecular kinetic isotope effects, and the exclusive cis-selectivity of cyclization, a mechanism involving a C-H activation motif has been proposed for this transformation. |
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Authors:
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Natalia Chernyak; Vladimir Gevorgyan |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. Date: 2008-03-22 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 130 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2008 Apr |
Date Detail:
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Created Date: 2008-04-23 Completed Date: 2008-06-17 Revised Date: 2008-12-15 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 5636-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Alkynes
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chemistry* Carbon / chemistry Catalysis Cyclization Fluorenes / chemistry Hydrogen / chemistry Models, Chemical Palladium / chemistry* Polycyclic Hydrocarbons, Aromatic / chemical synthesis* |
| Grant Support | |
ID/Acronym/Agency:
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GM-64444/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Alkynes; 0/Fluorenes; 0/Polycyclic Hydrocarbons, Aromatic; 1333-74-0/Hydrogen; 7440-05-3/Palladium; 7440-44-0/Carbon; 86-73-7/fluorene |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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