Strategies for oxidative synthesis of N-triflyl sulfoximines

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

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.

• Language: English
• Keywords: oxidation, N-trifluoromethylthio sulfoximines, N-triflyl sulfoximines, sodium hypochlorite pentahydrate
• 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: 2024
• Number of pages: Str. 30836-30843
• Numbering: Vol. 14, iss. 42
• PID: 20.500.12556/RUL-163178
• UDC: 547.415.3:546.22:542.943
• ISSN on article: 2046-2069
• DOI: 10.1039/D4RA04992F
• COBISS.SI-ID: 210006787
• Publication date in RUL: 03.10.2024

Record is a part of a journal

• Title: RSC advances
• Publisher: RSC Publishing
• ISSN: 2046-2069
• COBISS.SI-ID: 2513252

Licences

• License: CC BY-NC 3.0, Creative Commons Attribution-NonCommercial 3.0 Unported
• Link: http://creativecommons.org/licenses/by-nc/3.0/
• Description: You are free to reproduce and redistribute the material in any medium or format. You are free to remix, transform, and build upon the material. You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.

Secondary language

• Language: Slovenian
• Keywords: oksidacija, N-trifluorometiltio sulfoksimini, N-triflil sulfoksimini, natrijev hipoklorit pentahidrat

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0230
• Name: Organska kemija: sinteza, struktura in aplikacija

• Funder: ARRS - Slovenian Research Agency
• Name: Young Researcher Grant