A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

✍ Scribed by Kinzel, Tom; Zhang, Yong; Buchwald, Stephen L.

• Book ID: 118157146
• Publisher: American Chemical Society
• Year: 2010
• Tongue: English
• Weight: 608 KB
• Volume: 132
• Category: Article
• ISSN: 0002-7863
• DOI: 10.1021/ja1073799

✦ Synopsis

Boronic acids which quickly deboronate under basic conditions, such as polyfluorophenylboronic acid and fivemembered 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.