Document Detail


Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions.
MedLine Citation:
PMID:  22998540     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Changwu Zheng; Dian Wang; Shannon S Stahl
Publication Detail:
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:
Title:  Journal of the American Chemical Society     Volume:  134     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-10     Completed Date:  2013-03-01     Revised Date:  2013-10-17    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  16496-9     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Alkenes / chemistry
Boronic Acids / chemistry
Catalysis
Oxidation-Reduction
Palladium / chemistry
Polyenes / chemical synthesis*,  chemistry
Stereoisomerism
Grant Support
ID/Acronym/Agency:
R01 GM067173/GM/NIGMS NIH HHS; R01 GM67163/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Alkenes; 0/Boronic Acids; 0/Polyenes; 7440-05-3/Palladium
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Adolescents, Gangs, and Perceptions of Safety, Parental Engagement, and Peer Pressure.
Next Document:  Cutaneous adverse events associated with heparin.