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Palladium-Catalyzed β‑Mesylation of Simple Amide via Primary sp3 C–H Activation

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journal contribution
posted on 22.03.2017, 15:50 authored by Ren Zhao, Wenjun Lu
A β-mesylation of primary sp3 C–H bonds from simple amides with methanesulfonic anhydride (Ms2O) has been established successfully at 80 °C in a Pd­(OAc)2 (catalyst)/K2S2O8 (oxidant)/CF3CH2OH (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 SN2 processes.