Pd(II)-catalyzed primary-C(sp3)-H acyloxylation at room temperature

Raja K Rit; M Ramu Yadav; Akhila K Sahoo

doi:10.1021/ol301579q

Pd(II)-catalyzed primary-C(sp3)-H acyloxylation at room temperature

Org Lett. 2012 Jul 20;14(14):3724-7. doi: 10.1021/ol301579q. Epub 2012 Jul 5.

Authors

Raja K Rit¹, M Ramu Yadav, Akhila K Sahoo

Affiliation

¹ School of Chemistry, University of Hyderabad , Hyderabad, India.

PMID: 22765229
DOI: 10.1021/ol301579q

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.