Rhodium-catalyzed addition of arylboron compounds to nitriles, ketones, and imines

The rhodium-catalyzed addition reactions of sodium tetraphenylborate and arylboronic acids to nitriles, ketones, and imines were examined. The reaction of nitriles could be carried out efficiently in the presence of a catalyst system of [RhCl(cod)]2–dppp and H2O to give the corresponding monoarylated products selectively. Although unactivated ketones and imines are known to be poor electrophiles for rhodium-catalyzed arylation, the phenylation of them with use of sodium tetraphenylborate proceeded smoothly in the presence of [RhCl(cod)]2 and Rh(acac)(cod) as catalysts, respectively. The addition of NH4Cl was found to be crucial to effectively conduct the reaction of ketones and imines.

Graphical abstractNitriles, ketones, and imines efficiently undergo intermolecular phenylation with use of sodium tetraphenylborate under rhodium catalysis. The addition of H2O and NH4Cl is crucial to smoothly conduct the reaction of nitriles and of the latter two substrates, respectively.Figure optionsDownload full-size imageDownload as PowerPoint slide