The Microwave Assisted, Gold-Catalyzed Ritter-type Reaction

C323

Advances in amide synthesis has been vital to medicinal advancement, as the amide functional group is found in many of today’s life changing medications and used for treatment of HIV, cancer, hepatitis B, and much more. Our lab has recently developed methodology to couple benzylic alcohols with nucleophiles using gold(I) salts. Herein, we report the synthesis of secondary N-benzylamides by a microwave-assisted gold-catalyzed Ritter-type reaction of benzylic alcohols. Optimal reaction conditions were determined to be 5 mol % Ph₃PAuCl as the gold(I) catalyst and 5 mol % AgSbF₆ as the silver co-catalyst with microwave irradiation. Furthermore, our reaction methodology supports the growing literature of gold(I) having similar catalytic activity as the hydronium, a hard acid. Full details of catalyst loading investigations will be discussed, and extensive substrate scope explorations will be presented.