Document Detail


Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid.
MedLine Citation:
PMID:  22769742     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.
Authors:
Gary A Molander; Sarah L J Trice; Steven M Kennedy; Spencer D Dreher; Matthew T Tudge
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:  2012-07-06
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  134     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Jul 
Date Detail:
Created Date:  2012-07-18     Completed Date:  2012-10-29     Revised Date:  2013-07-22    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  11667-73     Citation Subset:  IM    
Affiliation:
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
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MeSH Terms
Descriptor/Qualifier:
Boronic Acids / chemistry*
Catalysis
Palladium / chemistry*
Grant Support
ID/Acronym/Agency:
R01 GM081376/GM/NIGMS NIH HHS; R01 GM081376/GM/NIGMS NIH HHS; S10 RR016640/RR/NCRR NIH HHS
Chemical
Reg. No./Substance:
0/Boronic Acids; 7440-05-3/Palladium
Comments/Corrections

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