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 ismediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicate that NH-tr...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 2; pp. 348 - 351
Main Authors Tota, Arianna, Zenzola, Marina, Chawner, Stephen J., St John-Campbell, Sahra, Carlucci, Claudia, Romanazzi, Giuseppe, Degennaro, Leonardo, Bull, James A., Luisi, Renzo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Functional groups
Oxidation
Physical Sciences
Science & Technology
Selectivity
Sulfides
Synthesis
Synthesis (chemistry)
MEDICINAL CHEMISTRY
CATALYZED NITRENE TRANSFER
SULFOXIDES
AMINATION
VERSATILE
KINETIC RESOLUTION
IMINATION
ARENES
ACYL
SULFIMIDES
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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 ismediated 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 (AcONH4)-N-15 affords N-15-labeled compounds.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc08891k