18922-63-9Relevant academic research and scientific papers
Silver-catalyzed imination of sulfoxides and sulfides
Gae, Young Cho,Bolm, Carsten
, p. 4983 - 4985 (2005)
(Chemical Equation Presented) Silver salts in the presence of a chelating ligand efficiently catalyze the stereospecific imination of sulfoxides and sulfides with sulfonylamides and Phl(OAc)2 to afford sulfoximines and sulfilimines, respectivel
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.
Copper-catalyzed imination of sulfoxides and sulfides
Liu, Yuanyuan,Wang, Hanying,Yang, Xianjin
supporting information, p. 4697 - 4702 (2019/07/22)
Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.
Sulfonylimino group transfer reaction using imino-λ3-iodanes with I2 as catalyst under metal-free conditions
Yoshimura, Akira,Makitalo, Cody L.,Jarvi, Melissa E.,Shea, Michael T.,Postnikov, Pavel S.,Rohde, Gregory T.,Zhdankin, Viktor V.,Saito, Akio,Yusubov, Mekhman S.
, (2019/03/19)
A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-λ3-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I2 under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with moderate to good yields. This facile transfer procedure of the sulfonylimino group can also be applied to triphenylphosphine to produce the respective iminotriphenylphosphoranes in high yields. According to the reaction mechanism studies, the process of imination from (N-tosylimino)-phenyl-λ3-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.
An unexpected cyclization reaction of tert-butyl o-trimethylsilylphenyl sulfoximine
Schmidt, Joerg Christoph,Adiwidjaja, Gunadi,Schaumann, Ernst
, p. 104 - 109 (2013/09/24)
An efficient one-pot synthesis of the title compound 5 starting from methyl phenyl sulfoximine is described. On attempted iododesilylation of this compound using iodine chloride, one methyl group on the silicon atom is formally replaced by the imino nitrogen to give a derivative 8 of the novel heterocyclic system 1,3,2-benzothiasilazole. ARKAT-USA, Inc.
[FeIII(F20-tpp)Cl] Is an effective catalyst for nitrene transfer reactions and animation of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions
Liu, Yungen,Che, Chi-Ming
experimental part, p. 10494 - 10501 (2010/10/21)
[FeIII(F20-tpp)Cl] (F20tpp = meso- tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95% yields), sulfimidation of sulfides (11 examples, 76-96% yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83% yields), and amination of saturated C-H bonds including that of cycloalkanes and adamantane (eight examples, 64-80% yields) can be accomplished by using 2 mol % [FeIII(F20- tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C-H bonds (three examples) can be reduced by up to 16fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion.
Rhodium-catalyzed imination of sulfoxides and sulfides: Efficient preparation of N-unsubstituted sulfoximines and sulfilimines
Okamura, Hiroaki,Bolm, Carsten
, p. 1305 - 1307 (2007/10/03)
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.
