Palladium-Catalyzed β‑Mesylation of Simple Amide via Primary sp<sup>3</sup> C–H Activation

2017-03-22T15:50:13Z (GMT) by Ren Zhao Wenjun Lu
A β-mesylation of primary sp<sup>3</sup> C–H bonds from simple amides with methanesulfonic anhydride (Ms<sub>2</sub>O) has been established successfully at 80 °C in a Pd­(OAc)<sub>2</sub> (catalyst)/K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> (oxidant)/CF<sub>3</sub>CH<sub>2</sub>OH (solvent) system. These amide substrates involve <i>N</i>-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 S<sub>N</sub>2 processes.