Document Detail


A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.
MedLine Citation:
PMID:  20858009     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and five-membered 2-heteroaromatic boronic acids, are especially challenging coupling partners for Suzuki-Miyaura reactions. Nevertheless, being able to use these substrates is highly desirable for a number of applications. Having found that monodentate biarylphosphine ligands can promote these coupling processes, we developed a precatalyst that forms the catalytically active species under conditions where boronic acid decomposition is slow. With this precatalyst, Suzuki-Miyaura reactions of a wide range of (hetero)aryl chlorides, bromides, and triflates with polyfluorophenyl, 2-furan, 2-thiophene, and 2-pyrroleboronic acids and their analogues proceed at room temperature or 40 °C in short reaction times to give the desired products in excellent yields.
Authors:
Tom Kinzel; Yong Zhang; Stephen L Buchwald
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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.    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  132     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-10-07     Completed Date:  2011-01-20     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  14073-5     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Boronic Acids / chemistry*
Catalysis
Palladium / chemistry*
Grant Support
ID/Acronym/Agency:
GM46059/GM/NIGMS NIH HHS; R01 GM046059/GM/NIGMS NIH HHS; R37 GM046059/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Boronic Acids; 5TWQ1V240M/Palladium
Comments/Corrections

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