Anže Zupanc (Author), Marjan Jereb (Author)

Abstract

This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF$_3$ congeners have been demonstrated.

Keywords

sulfidi;sulfoksimini;enolončna pretvorba;N-jodo sulfoksimini;sulfides;sulfoximines;one-pot;N-iodo sulfoximines;

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.544
COBISS: 58059779 Link will open in a new window
ISSN: 0022-3263
Views: 357
Downloads: 195
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Other data

Secondary language: Slovenian
Secondary keywords: sulfidi;sulfoksimini;enolončna pretvorba;N-jodo sulfoksimini;
Type (COBISS): Article
Source comment: This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.
Pages: str. 5991-6000
Volume: ǂVol. ǂ86
Issue: ǂiss. ǂ8
Chronology: 16 Apr. 2021
DOI: 10.1021/acs.joc.1c00292
ID: 12963092