NBS-activated cross-dehydrogenative esterification of carboxylic acids with DMSO

Abstract

The first N-bromosuccinimide (NBS)-promoted transition metal-free cross-dehydrogenative esterification of carboxylic acids with dimethyl sulfoxide (DMSO) has been disclosed for formal C–O formation via Pummerer-type rearrangement. These transformations employ readily available carboxylic acids as the nucleophile and DMSO as the sulfur-containing carbon source and solvent under mild conditions, affording valuable (methylsulfinyl)methyl esters with a broad substrate scope. Furthermore, the developed protocol provides an efficient and straightforward method for the preparation of deuterated (methylsulfinyl)methyl esters by use of deuterium-labelled DMSO as the reagent.