Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

“Cationic” Suzuki–Miyaura Coupling with Acutely Base-Sensitive Boronic Acids

“Cationic” Suzuki–Miyaura Coupling with Acutely Base-Sensitive Boronic Acids
Daniel R. Sanchez, Bufan Zhang, Brad P. Carrow, Liye Chen
Fast, base-promoted protodeboronation of polyfluoroaryl and heteroaryl boronic acids complicates their use in Suzuki–Miyaura coupling (SMC) because a base is generally required for catalysis. We report a “cationic” SMC method using a PAd3-Pd catalyst that proceeds at rt in the absence of a base or metal mediator. A wide range of sensitive boronic acids, particularly polyfluoroaryl substrates that are poorly compatible with classic SMC conditions, undergo clean coupling. Stoichiometric experiments implicate the intermediacy of organopalladium cations, which supports a long-postulated cationic pathway for transmetalation in SMC.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07687

DOI: 10.1021/jacs.7b07687

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