Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base

alpha-Hydroxyl amides are important skeleton and valuable intermediates that present in many natural products, pharmaceutical active compounds, and organic functional materials. The main methods for synthesis of alpha-hydroxyl amides are either through amidation of alpha-hydroxyl acids, or by reduction of alpha-keto amides. Herein, a convenient potassium hydroxide/dimethyl sulfoxide promoted aerobic oxidation reaction to prepare N-substituted alpha-hydroxyl phenylacetamides is reported in good to high yields. 21 corresponding products were obtained and characterized by H-1 NMR, C-13 NMR and HRMS. The molecular structure of 2-(2-bromophenyl)-2-hydroxy-N-(p-tolyl) acetamide (2a) was confirmed by using single-crystal X-ray analyses.