Transamidation via C-N bond cleavage of amides and tertiary amines

The C-N bond of tertiary amines was activated in the presence of a palladium catalyst and peroxide and subsequently reacted with tertiary amides to provide transamidated products in good yields. The protocol exhibited a broad substrate scope. The optimal conditions were determined as: PdCl2(2 mol%), KI (10 mol%), NH4Cl (10 mol%) and di-tert-butylperoxide (DTBP), in anisole at 100 degrees C.N-Benzoylglutarimide,N-phenyl-N-tosylbenzamide,N-Boc-N-phenylbenzamide and benzoyl saccharin were successfully coupled with tertiary amines. The palladium catalyst and DTBP are likely involved in the cleavage of the C-N bond of tertiary amines to provide the corresponding secondary amines.