Hypervalent Iodine Mediated Synthesis of Sulfinamidines from Sulfenamides

In this study, we present a novel, efficient method forthe oxidativeamination of sulfenamides using diacetoxyiodobenzene (PhI(OAc)(2)) and amines under basic conditions. This innovative techniquestreamlines the synthesis of sulfinamidines under mild, metal-freeconditions, achieving outstanding yields of up to 99%. Furthermore,we propose possible pathways that elucidate the observed molecularsequence of events in this reaction. This cutting-edge approach notonly advances the synthesis of valuable sulfinamidine compounds butalso expands the synthetic toolbox available to chemists, paving theway for future discoveries in organic synthesis and potential applicationsin medicinal chemistry.

Automated summary

In this study, a novel and efficient method for the oxidativeamination reaction of sulfenamides was developed using diacetoxyiodobenzene and amines under basic conditions. This technique simplifies the synthesis of sulfinamidines, achieving high yields up to 99% without the need for metal catalysts. Possible reaction pathways were proposed to explain the observed molecular sequence of events. This cutting-edge approach not only advances the synthesis of valuable sulfinamidine compounds, but also expands the synthetic toolbox available to chemists, paving the way for future discoveries in organic synthesis and potential applications in medicinal chemistry.