Imino-λ3-iodanes are useful nitrene precursors and effective oxidants in the reactions with various organic substrates. Most of the known reactions of imino-λ3-iodanes are carried in the presence of transition metal catalysts, required for the in-situ generation of active metal-nitrenoid species. Recently, several groups have reported the azirizination of olefines, C-H amination of alkanes, and imination of aldehydes using imino-λ3-iodanes under metal-free conditions. However, the imination of sulfides using imino-λ3-iodanes under metal-free condition is still unknown. Herein, we report the new reaction of metal-free transimination reaction of sulfides using imino-λ3-iodanes in the presence of catalytic amounts of elemental iodine. The transimination reactions of various alkyl or aryl sulfides proceed at room temperature to give the corresponding sulfimines in low to good yields. The reaction of allyl sulfides under similar conditions proceeds as [2,3]-sigmatropic rearrangement to give the corresponding allyl sulfonamides in good yields.

Metal-free imination of sulfides using tosyliminoiodane reagent

253rd National Meeting (2017)

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