Synthesis Of NH-sulfoximines From Sulfides By Chemoselective One ...

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers†

Arianna Tota,a Marina Zenzola,a Stephen J. Chawner,b Sahra St John-Campbell,b Claudia Carlucci,a Giuseppe Romanazzi,cd Leonardo Degennaro,a James A. Bull *b and Renzo Luisi *a Author affiliations

* Corresponding authors

a Department of Pharmacy – Drug Sciences, University of Bari, “A. Moro” Via E. Orabona 4, Bari 70125, Italy E-mail: [email protected]

b Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK E-mail: [email protected]

c DICATECh, Politecnico di Bari, Via E. Orabona 4, Bari 70125, Italy

d CNR NANOTEC−Istituto di Nanotecnologia, Campus Ecotekne, via Monteroni, 73100 Lecce, Italy

Abstract

Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicate that NH-transfer is likely to be first, followed by oxidation, but the reaction proceeds successfully in either order. A wide range of functional groups and biologically relevant compounds are tolerated. The use of AcO15NH4 affords 15N-labeled compounds.

• This article is part of the themed collection: Most cited articles from 2017

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