A General, One-Pot Method for the Synthesis of Sulfinic Acids from Methyl Sulfones

Abstract

A simple and efficient method for converting methyl sulfones to sulfinic acids is described. The process involves alkylation with a benzylic halide, followed by in situ elimination of the resulting styrene in the presence of excess base to yield a sulfinic acid in a single reaction process. The usefulness of the alkylation-elimination sequence is demonstrated by generating a variety of sulfinic acids from methyl sulfones. Late stage functionalization and ¹⁴C-labeling of several biologically active methyl sulfones were accessed via sulfinate intermediates.