| Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions. | |
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MedLine Citation:
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PMID: 22998540 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Pd-catalyzed aerobic oxidative coupling of vinylboronic acids and electronically unbiased alkyl olefins provides regioselective access to 1,3-disubstituted conjugated dienes. Catalyst-controlled regioselectivity is achieved by using 2,9-dimethylphenanthroline as a ligand. The observed regioselectivity is opposite to that observed from a traditional (nonoxidative) Heck reaction between a vinyl bromide and an alkene. DFT computational studies reveal that steric effects of the 2,9-dimethylphenanthroline ligand promote C-C bond formation at the internal position of the alkene. |
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Authors:
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Changwu Zheng; Dian Wang; Shannon S Stahl |
Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2012-09-28 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 134 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2012 Oct |
Date Detail:
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Created Date: 2012-10-10 Completed Date: 2013-03-01 Revised Date: 2013-04-16 |
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: 16496-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Alkenes
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chemistry Boronic Acids / chemistry Catalysis Oxidation-Reduction Palladium / chemistry Polyenes / chemical synthesis*, chemistry Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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R01 GM067173/GM/NIGMS NIH HHS; R01 GM67163/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Alkenes; 0/Boronic Acids; 0/Polyenes; 7440-05-3/Palladium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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