Sulfoximine N-functionalization with N-fluorobenzenesulfonamide

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

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.

• Jezik: Angleški jezik
• Ključne besede: sulfoximine, N-fluorobenzenesulfonamide, rearrangement, chemical reactions, column chromatography, nuclear magnetic resonance spectroscopy, organic reactions, thermodynamic properties
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2025
• Št. strani: Str. 15790-15803
• Številčenje: Vol. 90, iss. 44
• PID: 20.500.12556/RUL-175993
• UDK: 547.541
• ISSN pri članku: 0022-3263
• DOI: 10.1021/acs.joc.5c02077
• COBISS.SI-ID: 256400899
• Datum objave v RUL: 17.11.2025

Gradivo je del revije

• Naslov: Journal of organic chemistry
• Skrajšan naslov: J. org. chem.
• Založnik: American Chemical Society.
• ISSN: 0022-3263
• COBISS.SI-ID: 235287

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: sulfoksimin, N-fluorobenzensulfonamid, premestitev