Palladium-Catalyzed β-Mesylation of Simple Amide via Primary sp C-H Activation.

A β-mesylation of primary sp C-H bonds from simple amides with methanesulfonic anhydride (MsO) has been established successfully at 80 °C in a Pd(OAc) (catalyst)/KSO (oxidant)/CFCHOH (solvent) system. These amide substrates involve N-monosubstituted linear, branch, or cyclic alkanes, and electron-deficient benzyl compounds. The β-mesylated amide products can be converted easily to β-fluoroamides or β-lactams through inter- or intramolecular S2 processes.