Strategies for oxidative synthesis of N-triflyl sulfoximines

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

The oxidation of various structurally different N-trifluoromethylthio sulfoximines was investigated using different oxidizing agents and conditions. Mono- and disubstituted phenyl methyl and phenyl cyclopropyl N-trifluoromethylthio sulfoximines were oxidized with NaOCl·5H$_2$O in water, while sterically hindered substrates bearing bulkier alkyl chains or two phenyl rings required the addition of MeCN to the reaction mixture. Chloro-, bromo-, and cyano-substituted substrates, as well as substrates bearing the benzyl groups, required a completely different approach using m-CPBA in DCM. Each method was tested on a gram-scale, with almost no difference in yield or reaction profile. The methods were also tested on N-p-tolylthio sulfoximine where successful oxidation to the corresponding sulfone derivative was observed. Finally, the N-triflyl sulfoximines acquired in the oxidations were examined in terms of stability and reactivity in Suzuki–Miyaura and Sonogashira coupling reactions, as well as many others. The selective mono- and dinitration of 4-methoxyphenyl N-triflyl sulfoximine was demonstrated by using nitric and sulfuric acid. N-triflyl sulfoximines were found to be stable in concentrated aqueous NaOH and HCl solutions and at elevated temperatures.

• Jezik: Angleški jezik
• Ključne besede: oxidation, N-trifluoromethylthio sulfoximines, N-triflyl sulfoximines, sodium hypochlorite pentahydrate
• 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: 2024
• Št. strani: Str. 30836-30843
• Številčenje: Vol. 14, iss. 42
• PID: 20.500.12556/RUL-163178
• UDK: 547.415.3:546.22:542.943
• ISSN pri članku: 2046-2069
• DOI: 10.1039/D4RA04992F
• COBISS.SI-ID: 210006787
• Datum objave v RUL: 03.10.2024

Gradivo je del revije

• Naslov: RSC advances
• Založnik: RSC Publishing
• ISSN: 2046-2069
• COBISS.SI-ID: 2513252

Licence

• Licenca: CC BY-NC 3.0, Creative Commons Priznanje avtorstva-Nekomercialno 3.0 Nedoločena
• Povezava: https://creativecommons.org/licenses/by-nc/3.0/deed.sl
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Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: oksidacija, N-trifluorometiltio sulfoksimini, N-triflil sulfoksimini, natrijev hipoklorit pentahidrat

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0230
• Naslov: Organska kemija: sinteza, struktura in aplikacija

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Naslov: Young Researcher Grant