Issue 12, 2017

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
14 Dec 2016
Accepted
23 Jan 2017
First published
30 Jan 2017

Chem. Commun., 2017,53, 2064-2067

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

J. Lohier, T. Glachet, H. Marzag, A. Gaumont and V. Reboul, Chem. Commun., 2017, 53, 2064 DOI: 10.1039/C6CC09940H

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