One-pot synthesis of N-iodo sulfoximines from sulfides

Zupanc, Anže (author), Jereb, Marjan (author)

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.

• Language: English
• Keywords: sulfides, sulfoximines, one-pot, N-iodo sulfoximines, chemical reactions, isolation, mixtures, nuclear magnetic resonance spectroscopy
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2021
• Number of pages: Str. 5991-6000
• Numbering: Vol. 86, iss. 8
• PID: 20.500.12556/RUL-127256
• UDC: 547.544
• ISSN on article: 0022-3263
• DOI: 10.1021/acs.joc.1c00292
• COBISS.SI-ID: 58059779
• Publication date in RUL: 31.05.2021

Record is a part of a journal

• Title: Journal of organic chemistry
• Shortened title: J. org. chem.
• Publisher: American Chemical Society
• ISSN: 0022-3263
• COBISS.SI-ID: 235287

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: sulfidi, sulfoksimini, enolončna pretvorba, N-jodo sulfoksimini