A convenient synthesis of N-aryl benzamides by rhodium-catalyzed ortho-amidation and decarboxylation of benzoic acids

Abstract

The rhodium-catalyzed amidation of substituted benzoic acids with isocyanates by directed CH functionalization followed by decarboxylation to afford the corresponding N-aryl benzamides is demonstrated, in which the carboxylate serves as a unique, removable directing group. Notably, less common meta-substituted N-aryl benzamides are generated readily from more accessible para- or ortho-substituted groups by employing this strategy.

Keywords: CH activation; amidation; decarboxylation; homogeneous catalysis; synthetic methods.