Electrochemical imination of sulfoxides using N-aminophthalimide.
[reaction: see text] A novel electrochemical sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N-N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.
Siu
Tung
T
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Yudin
Andrei K
AK
D004563:Electrochemistry; D004579:Electron Transport; D007097:Imines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
D007097:Imines; D007202:Indicators and Reagents; C458259:N-aminophthalimide; D010797:Phthalimides; D013454:Sulfoxides