Sulfoximine N-functionalization with N-fluorobenzenesulfonamideTesten, Žan (Avtor) Podlipnik, Črtomir (Avtor) Jereb, Marjan (Avtor) sulfoximineN-fluorobenzenesulfonamiderearrangementchemical reactionscolumn chromatographynuclear magnetic resonance spectroscopyorganic reactionsthermodynamic propertiesAn 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.20252025-11-17 13:41:31Članek v reviji175993sl