Copper-mediated oxidative homocoupling and rearrangement of N-alkoxyamides: an efficient method for the preparation of aromatic esters

Abstract N -Alkoxyamides are successfully converted into their corresponding esters in a moderate to satisfactory yields via copper-catalyzed oxidative homocoupling and Heron rearrangement. The process tolerates a wide variety of functional groups and allows the synthesis of sterically hindered ester products not readily accessible by traditional acylation chemistry. A radical-mediated pathway has been tentatively proposed for the oxidative process.