Abstract
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 H 2O 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 NH 4Cl was found to be crucial to effectively conduct the reaction of ketones and imines.
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