Document Detail


Cross-Coupling of Diarylborinic Acids and Anhydrides with Arylhalides Catalyzed by a Phosphite/N-heterocyclic Carbene Co-supported Palladium Catalyst System.
MedLine Citation:
PMID:  22860711     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A highly efficient cross-coupling of diarylborinic acids and anhydrides with aryl chlorides and bromides has been effected by using a palladium catalyst system co-supported by a strong σ-donor N-heterocyclic carbene (NHC), N,N'-bis(2,6-diisopropylphenyl) imidazol-2-ylidene, and a strong π-acceptor phosphite, triphenylphosphite, in tert-BuOH in the present of K3PO4•3H2O. Unsymmetrical biaryls with a variety of functional groups could be obtained in good to excellent yields using as low as 0.01, 0.2-0.5 and 1mol% palladium loadings for aryl bromides, activated and deactivated aryl chlorides, respectively, under mild conditions. A ligand synergy between the σ-donor NHC and the π-acceptor phosphite in the Pd/NHC/P(OPh)3 catalytic system has been proposed to be responsible for the high efficacy to arylchlorides in the cross-coupling. A scalable and economical process has therefore been developed for synthesis of Sartan biphenyl from the Pd/NHC/P(OPh)3 catalyzed cross-coupling of di(4-methylphenyl)borinic acid with 2-chlorobenzonitrile.
Authors:
Xiaofeng Chen; Haihua Ke; Yao Chen; Changwei Guan; Gang Zou
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-8-6
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2012 Aug 
Date Detail:
Created Date:  2012-8-6     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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