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Issue 2, 2017
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Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

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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.

Graphical abstract: Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

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Article information


Submitted
07 Nov 2016
Accepted
01 Dec 2016
First published
01 Dec 2016

Chem. Commun., 2017,53, 348-351
Article type
Communication

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

A. Tota, M. Zenzola, S. J. Chawner, S. S. John-Campbell, C. Carlucci, G. Romanazzi, L. Degennaro, J. A. Bull and R. Luisi, Chem. Commun., 2017, 53, 348
DOI: 10.1039/C6CC08891K

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