Atmospheric Oxygen Facilitated Oxidative Amidation to α-Ketoamides and Unusual One Carbon Degradative Amidation to N -Alkyl Amides.

A mild, transition-metal-free novel synthetic approach for the construction of C═O and C-N bonds has been demonstrated. Easily accessible gem -dibromoalkenes under similar conditions form oxidative amidation product α-ketoamides and unusual degradative amidation product N -alkyl amides by simply changing the amine substitute. Atmospheric air containing molecular oxygen proved to be an ideal oxidant for an amidation reaction. Under similar conditions, the electron-deficient gem -dibromoalkenes play a dual role with different formamides forming novel oxidative amidation products and by the state of art neighboring group participation of amine to unusual one-carbon degradative amidation products.