Strategies for oxidative synthesis of N-triflyl sulfoximinesTesten, Žan (Avtor) Jereb, Marjan (Avtor) oxidationN-trifluoromethylthio sulfoximinesN-triflyl sulfoximinessodium hypochlorite pentahydrateThe 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.20242024-10-03 12:52:34Članek v reviji163178UDK: 547.415.3:546.22:542.943ISSN pri članku: 2046-2069DOI: 10.1039/D4RA04992FCOBISS_ID: 210006787sl