期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 40, 页码 14073-14075出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja1073799
关键词
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资金
- NIH [GM46059]
- NSF [CHE 9808061, DBI 9729592]
- Alexander von Humboldt Foundation
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 degrees C in short reaction times to give the desired products in excellent yields.
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