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

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-t...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017, Vol.53 (2), p.348-351
Main Authors: Tota, Arianna, Zenzola, Marina, Chawner, Stephen J, John-Campbell, Sahra St, Carlucci, Claudia, Romanazzi, Giuseppe, Degennaro, Leonardo, Bull, James A, Luisi, Renzo
Format: Article
Language:English
Subjects:
Functional groups
Oxidation
Selectivity
Sulfides
Synthesis
Synthesis (chemistry)
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Summary: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 AcO NH affords N-labeled compounds.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc08891k