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

Abstract

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 °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.