Sulfoxide-mediated Umpolung of alkali halide salts

Org Biomol Chem. 2012 Jun 14;10(22):4327-9. doi: 10.1039/c2ob25459j. Epub 2012 Apr 3.

Abstract

A new protocol for the direct two-electron oxidative Umpolung of alkali halide salts is reported. This procedure, relying on the use of a commercially available sulfoxide as the oxidant, allows the electrophilic halogenation of carbonyl compounds as well as halolactonisation reactions to proceed from the corresponding sodium salts, at room temperature and under mild conditions.