Synthesis of Carboxylic Acids from Benzamide Precursors Using Nickel Catalysis

A. N-Methyl-N-phenyl benzamide (3). A single-necked (24/40 joint) 500 mL round-bottomed flask is equipped with a Teflon-coated magnetic stir bar (3 cm, oval-shaped). The flask is dried in an oven (105 °C) for 16 h. The flask is brought out of the oven, sealed immediately with a rubber septum, and allowed to cool to room temperature (23 °C) in a desiccator (Note 2). The flask is purged with argon by connecting to an argon manifold using a needle (18G), and via another needle (18G) to a gas outlet terminating in an oil bubbler. The atmosphere is maintained under a slight positive pressure of argon for the duration of the reaction (Note 3). The flask is then charged with triethylamine (6.5 mL, 47 mmol, 1.3 equiv) (Note 4) using a plastic syringe Et3N CH2Cl2, 0 °C to 23 °C 1