20.500.12556/RUL-163178 Strategies for oxidative synthesis of N-triflyl sulfoximines 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. oxidation N-trifluoromethylthio sulfoximines N-triflyl sulfoximines sodium hypochlorite pentahydrate oksidacija N-trifluorometiltio sulfoksimini N-triflil sulfoksimini natrijev hipoklorit pentahidrat true false true Angleški jezik Slovenski jezik Članek v reviji 2024-10-03 12:52:34 2024-10-03 12:52:34 2024-10-04 04:15:58 0000-00-00 00:00:00 2024 0 0 Str. 30836-30843 iss. 42 Vol. 14 2024 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547.415.3:546.22:542.943 2046-2069 10.1039/D4RA04992F 210006787 RAZ_Testen_Zan_2024.pdf RAZ_Testen_Zan_2024.pdf 1 1F4FC8CA931CB9DB2B10903566134049 2722734a02580d8f5409af96932eae15c786f0f70be9f28eb054df4cddabf549 6c37076f-8176-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=192705 https://pubs.rsc.org/en/content/articlelanding/2024/ra/d4ra04992f 1 7037bcb4-8175-11ef-b232-0050569b8976 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=192704 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0