Expanding the Scope of Hypervalent Iodine Reagents in the Synthesis of Sulfinamides from Sulfenamides

Abstract

This study presents a novel, efficient method for the synthesis of sulfinamidines via oxidative amination of sulfenamides using diacetoxyiodobenzene (PhI(OAc)2) and secondary amines under basic conditions. The technique achieves outstanding yields of up to 99%, streamlining the process under mild and metal-free conditions. In addition, two possible pathways are proposed to explain the observed molecular sequence of events in this reaction. The advanced approach expands the synthetic toolbox available to chemists, enabling the synthesis of valuable sulfinamidine compounds, and opening up potential applications in medicinal chemistry. Overall, this study highlights the potential of hypervalent iodine-mediated methods for efficient and streamlined organic synthesis.

Redox-Neutral Synthesis of Sulfilimines through the S-Alkylation of Sulfenamides

“…To the best of our knowledge, reports on transition-metal-free S-alkylation of sulfenamides under alkaline conditions are scarce in the literature . Our research group has tackled the challenging task of effecting S-alkylation of sulfenamides under basic and oxidant-free conditions, through systematic optimization of reaction conditions, by synthesizing sulfenamides bearing a range of tunable and steric groups in order to achieve precise control over regioselectivity, in keeping with our dedication to exploring the properties of sulfenamides …”