91146-71-3Relevant academic research and scientific papers
Imination of sulfoxides mediated by IBX with Sc(OTf)3 as catalyst
Yan, Tu-Hsin,Ananthan, Bakthavachalam
supporting information, p. 946 - 953 (2018/03/21)
Herein we utilized, for the first time, 2-iodoxybenzoate along with scandium triflate as a specific oxidant for PhthNH2 to create sulfoximines. This method efficiently effects imination of aryl, benzyl, cyclic and alkyl substituted S?O bonds with good to excellent yields. In addition, sterically encumbered sulfoxides have been studied and found that the present protocol is the worthy choice. This facile method does not require either inert atmosphere or anhydrous solvents.
Development of electrochemical processes for nitrene generation and transfer
Siu, Tung,Picard, Christine J.,Yudin, Andrei K.
, p. 932 - 937 (2007/10/03)
(Chemical Equation Presented) An electrochemical strategy for running nitrogen-transfer reactions on chemically inert anode surfaces has been developed. The generation and trapping of highly reactive nitrene-transfer reagents can be accomplished under mild conditions on platinum electrodes. The key factor that accounts for the high levels of chemoselectivity in this process is the phenomenon of overpotential. We have found that molecules that are similar in terms of propensity toward oxidation can be differentiated on the basis of their affinity to a given electrode surface. Thereby, reactive species can be selectively generated in the presence of acceptor molecules of interest. Specifically, a wide range of structurally dissimilar olefins can be transformed into the corresponding aziridines in the presence of N-aminophthalimide. Likewise, nitrene generation in the presence of sulfoxides leads to their chemoselective transformation into the corresponding sulfoximines. In this paper we discuss the underlying mechanistic foundation of these reactions.
Electrochemical Imination of Sulfoxides Using N-Aminophthalimide
Siu, Tung,Yudin, Andrei K.
, p. 1839 - 1842 (2007/10/03)
(Equation Presented) 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.
