| A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids. | |
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MedLine Citation:
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PMID: 20858009 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Tom Kinzel; Yong Zhang; Stephen L Buchwald |
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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. |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 132 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2010 Oct |
Date Detail:
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Created Date: 2010-10-07 Completed Date: 2011-01-20 Revised Date: 2013-05-01 |
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: 14073-5 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Boronic Acids
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chemistry* Catalysis Palladium / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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GM46059/GM/NIGMS NIH HHS; R01 GM046059-20/GM/NIGMS NIH HHS; R37 GM046059/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Boronic Acids; 7440-05-3/Palladium |
| Comments/Corrections | |
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