Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for λ6-sulfanenitrile intermediates

We report a new procedure for the preparation of NH-sulfoximines from sulfides using PIDA as an oxidant and ammonium carbamate as the ammonia source. Excellent yields were obtained with a wide range of sulfides. The formation of acetoxy- and methoxy-λ6-sulfanenitrile as intermediates was proposed, b...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 12; pp. 2064 - 2067
Main Authors Lohier, Jean-François, Glachet, Thomas, Marzag, Hamid, Gaumont, Annie-Claude, Reboul, Vincent
Format Journal Article
LanguageEnglish
Published Royal Society of Chemistry 07.02.2017
Subjects
Chemical Sciences
Medicinal Chemistry
Organic chemistry
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Summary:We report a new procedure for the preparation of NH-sulfoximines from sulfides using PIDA as an oxidant and ammonium carbamate as the ammonia source. Excellent yields were obtained with a wide range of sulfides. The formation of acetoxy- and methoxy-λ6-sulfanenitrile as intermediates was proposed, both of which were converted to the NH-sulfoximine by the action of the solvent. The structure of these intermediates was confirmed by 1H, 13C and 15N NMR and HRMS analysis.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc09940h