Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis of β-Amidovinyl Sulfones

beta-Amido sulfone motif reprents a particularly useful scaffold for the biologically active molecules. The hydrogenation of beta-amidovinyl sulfon is an alternative method to synthesize beta-amido sulfone. Herein, one electrochemical method to synthesize beta-amido sulfone using sodium sulfites and tertiary amines as substrates is presented. Only E-configurations of beta-amidovinyl sulfonyl were synthesized under metal catalyst- and oxidant-free condition. Cyclic voltammetry (CV) and control experiments indicate that this electrosynthesis reaction goes through a radical process which the sulfonyl radical adds to enamine to form the carbon radical.

Automated summary

The beta-amido sulfone motif is a useful scaffold for biologically active molecules, and the hydrogenation of beta-amidovinyl sulfon is an alternative method for synthesis. This study presents an electrochemical method using sodium sulfites and tertiary amines as substrates to synthesize beta-amido sulfone, with E-configurations produced under metal catalyst- and oxidant-free conditions. Cyclic voltammetry and control experiments suggest that the electrosynthesis reaction proceeds through a radical process involving the addition of a sulfonyl radical to an enamine to form a carbon radical.