A methodology for the synthesis of sulfonyl hydrazides mediated by hypervalent iodine is described. Taking advantage of the umpolung properties of hypervalent iodine reagents, the polarity of sodium sulfinate salts is reversed, and a key intermediate is generated and reacted with mono- and disubstituted hydrazines. To highlight the practical utility of this protocol, a diverse range of sulfonyl hydrazides were synthesized in yields up to 62%. Furthermore, a gram-scale reaction was performed, showing the robustness of the procedure. Mechanistic studies, including DFT calculations, were performed and the bioactivity of the generated compounds was evaluated.
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