Directing Influence of Proximal Boron Functionalities on the S-Alkylation of Sulfenic Acid Anions: An Experimental and Computational Study.

The S-functionalization chemistry of sulfenic acid anions, also known as sulfenate anions, represents an emerging method for the preparation of sulfoxides. Nearby functional groups can often influence the S-functionalization chemistry of sulfenate anions through nonbonding interactions. Recently, several reports have illustrated the combination of the Lewis acidity of trivalent boron and Lewis basicity of sulfinyl groups to perform valuable chemistry, but limited experimental investigations into the Lewis acid/Lewis base complex between sulfenate anions and trivalent boron functionalities have been conducted.