Copper catalysts have received broad interests and utilities in both academy and industry for their many advantages such as ready availability,economy,high activity,high efficiency,and low toxicity.Besides,due to their high capacity in dioxygen activation and by using oxygen or air as the green oxidant,coppers are particularly superior catalysts or co-catalysts in cross-dehydrogenative couplings (CDC),C-H activations and subsequent oxidative couplings with C-H and heteroatom-H compounds,and also the aerobic alcohol oxidations for aldehydes,ketones,and fine chemical synthesis.Although having been widely adopted in other methodologies for amine and amide derivative synthesis,the advantageous copper catalysts were seldom used in N-alkylation of amines/amides and alcohols in the past.Based on our previous aerobic N-alkyaltion studies,1 we deduce copper may also be a promising catalyst in the reaction for its potential in aerobic alcohol oxidation.Indeed,Cu can catalyze the N-alkylation of amides and amines with alcohols more efficiently under air than under nitrogen.Based on our detailed mechanistic studies and also supported by the literature,we propose that the newly-proposed aerobic relay race mechanism should be the most possible and a more rational mechanism for the reaction,and that the previously-concluded borrowing hydrogen-type mechanisms in aerobic and anaerobic Cu-catalyzed N-alkylation reactions were possibly wrong.3