Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols

We report the first example of copper-catalyzed alpha-alkylation of acetamides with alcohols via a borrowing hydrogen strategy. Catalyzed by the in situ-generated copper particles, acetamides and various substituted benzyl or alkyl alcohols were transformed into functionalized amides in good yields with excellent selectivity. Compared with previous work, this process is simple using commercially available Cu(OAc)(2) as a precatalyst, without an additional ligand or a metal complex, and easier. Mechanistic studies revealed that aldehyde and alpha,beta-unsaturated amides were the intermediates of this reaction and also disclosed the role of copper in alcohol dehydrogenation and C=C bond hydrogenation.