TBHP Mediated C-N Bond Cleavage of Tertiary Amines toward the Synthesis of Oxalamides and α,β-Epoxy Amides.

An efficient and convenient method for the synthesis of oxalamides by the reaction of β-ketoamides with tertiary amines and TBHP was developed. A variety of β-ketoamides and tertiary amines substrates were well-tolerated in this transformation. Based on the control experiments, a plausible mechanism for this reaction was proposed that involved the tandem oxidation/amination process. In addition, α,β-epoxy amides could be obtained by adjusting the reaction conditions.