Pd(II)-Catalyzed Primary-C(sp³)–H Acyloxylation at Room Temperature

With the aid of a novel S-methyl-S-2-pyridyl-sulfoximine (MPyS) directing group (DG), the unactivated primary β-C(sp3)–H bond of MPyS-N-amides oxidizes at room temperature. The catalytic conditions are applicable to the diacetoxylation of primary β,β′-C(sp3)–H bonds, and the carboxylic acid solvent is pivotal in the formation of the C–O bond. The MPyS-DG cleaves from the oxidation products and is recovered. This method provides convenient access to α,α′-disubstituted-β-hydroxycarboxylic acids.