18922-62-8Relevant academic research and scientific papers
Rhodium-catalyzed imination of sulfoxides and sulfides: Efficient preparation of N-unsubstituted sulfoximines and sulfilimines
Okamura, Hiroaki,Bolm, Carsten
, p. 1305 - 1307 (2004)
The Rh(II)-catalyzed imination of sulfoxides and sulfides using [Rh 2(OAc)4] as a catalyst and trifluoroacetamide or sulfonylamides in combination with iodobenzene diacetate and magnesium oxide affords sulfoximines and sulfilimines, respectively, in a stereospecific manner.
Iron-catalyzed imination of sulfoxides and sulfides
Mancheno, Olga Garcia,Bolm, Carsten
, p. 2349 - 2352 (2006)
The Fe(III)-catalyzed imination of sulfoxides and sulfides with sulfonylamides in the presence of iodinanes has been investigated. The best results were obtained when Fe(acac)3 was used as a catalyst in combination with iodosylbenzene, providin
Catalytic Chemoselective Sulfimidation with an Electrophilic [CoIII(TAML)]?-Nitrene Radical Complex**
van Leest, Nicolaas P.,van der Vlugt, Jarl Ivar,de Bruin, Bas
supporting information, p. 371 - 378 (2020/12/01)
The cobalt species PPh4[CoIII(TAMLred)] is a competent and stable catalyst for the sulfimidation of (aryl)(alkyl)-substituted sulfides with iminoiodinanes, reaching turnover numbers up to 900 and turnover frequencies of 640 min?1 under mild and aerobic conditions. The sulfimidation proceeds in a highly chemoselective manner, even in the presence of alkenes or weak C?H bonds, as supported by inter- and intramolecular competition experiments. Functionalization of the sulfide substituent with various electron-donating and electron-withdrawing arenes and several alkyl, benzyl and vinyl fragments is tolerated, with up to quantitative product yields. Sulfimidation of phenyl allyl sulfide led to [2,3]-sigmatropic rearrangement of the initially formed sulfimide species to afford the corresponding N-allyl-S-phenyl-thiohydroxylamines as attractive products. Mechanistic studies suggest that the actual nitrene transfer to the sulfide proceeds via (previously characterized) electrophilic nitrene radical intermediates that afford the sulfimide products via electronically asynchronous transition states, in which SET from the sulfide to the nitrene radical complex precedes N?S bond formation in a single concerted process.
Metal-Free Benzylic C?H Amination via Electrochemically Generated Benzylaminosulfonium Ions
Hayashi, Ryutaro,Shimizu, Akihiro,Song, Yetao,Ashikari, Yosuke,Nokami, Toshiki,Yoshida, Jun-Ichi
supporting information, p. 61 - 64 (2017/01/09)
Electrochemical oxidation of toluene derivatives in the presence of N-tosyldiphenylsulfilimine gave the corresponding benzylaminosulfonium ions, which were treated with tetrabutylammonium iodide under non-electrolytic conditions to give N-tosylbenzylamines. The transformation serves as a metal- and chemical-oxidant-free method for benzylic C?H amination. Because of high oxidation potential of N-tosyldiphenylsulfilimine the present method can be applied to synthesis of various benzylamines from functionalized toluene derivatives.
A versatile and highly reactive polyfluorinated hypervalent iodine (III) compound
Schaefer, Sascha,Wirth, Thomas
supporting information; experimental part, p. 2786 - 2789 (2010/07/06)
(Figure Presented) Hyper-reactive: A highly reactive, fully fluorinated hypervalent iodine reagent (see formula) mediates new transformations (e.g. the one-pot conversion of sulfides to sulfoximines) and serves as a stoichiometric oxidant in well-established reactions (e.g. C-C bond cleavage and the conversion of alcohols into aldehydes).
