Pd(II)-catalyzed primary-C(sp < sup > 3 < /sup > )-H acyloxylation at room temperature

Abstract

With the aid of a novel S-methyl-S-2-pyridyl-sulfoximine (MPyS) directing group (DG), the unactivated primary β-C(sp 3)-H bond of MPyS-N-amides oxidizes at room temperature. The catalytic conditions are applicable to the diacetoxylation of primary β,β′-C(sp 3)-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. © 2012 American Chemical Society.