Sulfoximine N-functionalization with N-fluorobenzenesulfonamide

Testen, Žan (author), Podlipnik, Črtomir (author), Jereb, Marjan (author)

An operationally simple, convenient, mild, metal-free, and scalable transformation of sulfoximines with N-fluorobenzenesulfonamide is presented. A wide range of structurally different NH-sulfoximines were prepared and reacted with N-fluorobenzenesulfonamide in the presence of TMP (2,2,6,6-Tetramethylpiperidine) and in the environmentally friendly EtOAc to obtain the desired products, mostly in yields above 75%. The method also supports various amine, hydrazide, phenol, and amino acid substrates as well as scale-up to gram reactions with minimal to no modification of the process. The products formed from the sulfoximines were structurally analyzed by NMR and X-ray crystallography and investigated for their stability and further reactivity as substrates in Suzuki-Miyaura coupling, methylation, and bromination reactions. In addition, DFT calculations were carried out with regard to the energy profile and mechanism of the reaction.

• Language: English
• Keywords: sulfoximine, N-fluorobenzenesulfonamide, rearrangement, chemical reactions, column chromatography, nuclear magnetic resonance spectroscopy, organic reactions, thermodynamic properties
• 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: 2025
• Number of pages: Str. 15790-15803
• Numbering: Vol. 90, iss. 44
• PID: 20.500.12556/RUL-175993
• UDC: 547.541
• ISSN on article: 0022-3263
• DOI: 10.1021/acs.joc.5c02077
• COBISS.SI-ID: 256400899
• Publication date in RUL: 17.11.2025

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: sulfoksimin, N-fluorobenzensulfonamid, premestitev