452898-04-3Relevant academic research and scientific papers
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.
I2-Catalyzed N-Sulfonylation of Sulfoximines with Sulfinates in Water at Room Temperature
Zheng, Wenting,Tan, Mingchao,Yang, Lu,Zhou, Lihong,Zeng, Qingle
, p. 1764 - 1768 (2020/03/13)
An oxidative coupling of NH-sulfoximines and arylsulfinates catalyzed by of I2 and H2O2 affords N-sulfonyl sulfoximines. The reaction proceeds under aerobic conditions in water at room temperature. The merits of this proto
Synthetic method of N-aryl sulfone sulfoximine
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Paragraph 0009-0013; 0041-0045, (2019/12/25)
Sulfoximines have a wide range of applications in organic chemistry, medicinal chemistry, agricultural chemistry, sulfimides are related to the medicinal activity of various organisms, such as antiarrhythmic, antispasmodic, antiasthmatic and antiviral act
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.
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).
Iron(ii) triflate as an efficient catalyst for the imination of sulfoxides
Mancheno, Olga Garcia,Dallimore, Jonathan,Plant, Andrew,Bolm, Carsten
supporting information; experimental part, p. 2429 - 2432 (2009/10/23)
The challenging imination of benzyl-, sterically demanding alkyl-, and heteroaryl-substituted sulfoxides has been studied. Iron(II) triflate was identified as a highly efficient and robust catalyst for sulfur imination reactions. A variety of sulfoxides a
Comparative study of metal-catalyzed iminations of sulfoxides and sulfides
Mancheno, Olga Garcia,Bolm, Carsten
, p. 6674 - 6681 (2008/03/15)
A comparative study of the imination of sulfur compounds with various metal catalysts in combination with isolated or in situ generated iminoiodinanes (PhI=NR) as nitrogen sources is presented. The influence of the metal catalyst towards the imination of a variety of substituted sulfoxides has been evaluated. Moreover, the effect of the different oxidation states of sulfur on the reactivity and selectivity of the nitrogen transfer redox process in the formation of sulfilimines and sulfoximines was studied. Depending on both the specific metal catalyst as well as the employed nitrene precursor, the sulfide/sulfoxide imination ratio varied in transformations of thianthrene-5-oxide and substituted para-thio phenylsulfoxides.
Iron-catalyzed imination of sulfoxides and sulfides
Mancheno, Olga Garcia,Bolm, Carsten
, p. 2349 - 2352 (2007/10/03)
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
Silver-catalyzed imination of sulfoxides and sulfides
Gae, Young Cho,Bolm, Carsten
, p. 4983 - 4985 (2007/10/03)
(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
Metal-free imination of sulfoxides and sulfides
Cho, Gae Young,Bolm, Carsten
, p. 8007 - 8008 (2007/10/03)
Using a nitrogen transfer agent obtained in situ by mixing of NsNH 2 and PhI(OAc)2, various N-nosyl sulfoximines and N-nosyl sulfilimines have been prepared under metal-free conditions starting from the corresponding sulfoxides and s
