Synthesis of cyclic sulfonamides via intramolecular copper-catalyzed reaction of unsaturated iminoiodinanes.
Olefinic primary sulfonamides were treated with iodobenzene diacetate and potassium hydroxide in methanol to give intermediate iminoiodinanes. Catalytic copper(I) or (II) triflate then provided intramolecular nitrene delivery leading to aziridine formation except in one case where a rare copper-catalyzed C-H insertion was observed. The aziridines could be opened by various nucleophiles (methanol, thiophenol, allylmagnesium bromide, benzylamine) to give the corresponding substituted cyclic sulfonamides.
Dauban
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Institut de Chimie des Substances Naturelles, C. N. R. S., F-91198 Gif-sur-Yvette, France. philippe.dauban@icsn.cnrs-gif.fr
Dodd
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D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D003300:Copper / Q000737:chemistry* / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D010128:p-Aminoazobenzene / Q000031:analogs & derivatives / Q000737:chemistry; D044482:Benzeneacetamides
D001388:Aziridines; D003300:Copper; D004791:Enzyme Inhibitors; D006574:Heterocyclic Compounds, 2-Ring; D013449:Sulfonamides; D010128:p-Aminoazobenzene; C003359:sulfamidochrysoidine; D044482:Benzeneacetamides