130567-06-5Relevant academic research and scientific papers
An increase in the cooperative catalytic performance of SBA-15 and TFE in selective oxidation of organic sulfides
Rostamnia, Sadegh,Doustkhah, Esmail,Bahrami, Kiumars,Amini, Soraya
, p. 334 - 337 (2015)
In this paper, trifluoroethanol (TFE) was confined into SBA-15 and compared with its similar non-fluorous systems in the metal-free oxidation of sulfides to sulfoxides in the presence of H2O2. This catalytic system successfully perfo
Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
Zhao, Bin,Hammond, Gerald B.,Xu, Bo
supporting information, (2021/09/13)
We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides
Lee, Sunwoo,Park, Jin Kyu
, p. 13790 - 13799 (2021/10/12)
The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.
Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications
Wang, Lei,Chen, Mingjie,Zhang, Peichao,Li, Wenbo,Zhang, Junliang
, p. 3467 - 3473 (2018/03/13)
Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.
Post-synthetically modified SBA-15 with NH2-coordinately immobilized iron-oxine: SBA-15/NH2-FeQ3 as a Fenton-like hybrid catalyst for the selective oxidation of organic sulfides
Golchin Hosseini, Habib,Rostamnia, Sadegh
, p. 619 - 627 (2017/12/28)
A new modified SBA-15 meso-material with NH2-coordinately immobilized "iron-oxine" was fabricated by stepwise covalent grafting of -NH2 and then NH2-coordinate immobilization of tris(8-quinolinolato)iron onto the channels of SBA-15. The structural properties and chemical nature of SBA-15/NH2-FeQ3 were characterized by FTIR, scanning electron microscopy (SEM), SEM-EDX/mapping, transmission electron microscopy (TEM), low angle X-ray diffraction (L-XRD), thermal gravimetric analysis (TGA), N2-adsorption-desorption isotherms (BET) and atomic absorption spectroscopy (AAS). A Fenton-like green and eco-friendly procedure for the catalytic oxidation of aromatic organic sulfides to sulfones using H2O2 was investigated for the synthesised Fe/SBA-15 catalyst. This porous catalyst was found to be reusable for ten runs without appreciable change in the activity, or the composition of the catalyst.
Visible-Light-Driven Silver-Catalyzed One-Pot Approach: A Selective Synthesis of Diaryl Sulfoxides and Diaryl Sulfones
Kim, Dong Hyuk,Lee, Juyoung,Lee, Anna
supporting information, p. 764 - 767 (2018/02/09)
An efficient one-pot approach for the synthesis of diaryl sulfoxides and diaryl sulfones using aryl thiols and aryl diazonium salts was developed. The use of a visible-light-driven silver catalysis and the subsequent singlet-oxygen-induced oxidation enabled selective synthesis of sulfoxides and sulfones in the absence of a photocatalyst. The reactions were carried out under mild reaction conditions; the desired products were obtained under air atmosphere at room temperature.
Palladium-Catalyzed Arylation of Aryl Sulfenate Anions with Aryl Bromides under Mild Conditions: Synthesis of Diaryl Sulfoxides
Jiang, Hui,Jia, Tiezheng,Zhang, Mengnan,Walsh, Patrick J.
supporting information, p. 972 - 975 (2016/03/15)
A palladium-catalyzed arylation of aryl sulfenate anions generated from aryl 2-(trimethylsilyl)ethyl sulfoxides and CsF has been developed. This protocol is effective for the synthesis of diaryl sulfoxides and heteroaryl aryl sulfoxides under mild conditions employing aryl bromides. Various functional groups, including those with acidic protons, are well tolerated.
Tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts
Gelat, Fabien,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Perrio, Stéphane
supporting information, p. 2011 - 2016 (2015/06/23)
The present report describes an efficient and clean generation of sulfenate salts (R1SO-) by pyrolysis of readily available tert-butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium-catalyzed cross-coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple C-S bond-forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di-tert-butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2-) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.
Palladium catalyzed diaryl sulfoxide generation from aryl benzyl sulfoxides and aryl chlorides
Jia, Tiezheng,Zhang, Mengnan,Sagamanova, Irina K.,Wang, Carol Y.,Walsh, Patrick J.
supporting information, p. 1168 - 1171 (2015/03/14)
Diaryl sulfoxides are synthesized from aryl benzyl sulfoxides and aryl chlorides via three sequential catalytic cycles all promoted by a NiXantPhos-based palladium catalyst. The key step is S-arylation of a sulfenate anion. An air- and moisture-stable precatalyst derived from NiXantPhos efficiently facilitates the transformation. Various functional groups, including those with acidic protons, were tolerated. This method can also be extended to methyl and dibenzyl sulfoxides substrates.
Diaryl sulfoxides from aryl benzyl sulfoxides: A single palladium-catalyzed triple relay process
Jia, Tiezheng,Bellomo, Ana,Montel, Sonia,Zhang, Mengnan,El Baina, Kawtar,Zheng, Bing,Walsh, Patrick J.
supporting information, p. 260 - 264 (2014/01/17)
A novel approach to produce diaryl sulfoxides from aryl benzyl sulfoxides is reported. Optimization of the reaction conditions was performed using high-throughput experimentation techniques. The [Pd(dba)2]/NiXantPhos catalyst system successfully promotes a triple relay process involving sulfoxide α-arylation, C-S bond cleavage, and C-S bond formation. The byproduct benzophenone is formed by an additional palladium-catalyzed process. It is noteworthy that palladium-catalyzed benzylative C-S bond cleavage of sulfoxides is unprecedented. A wide range of aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides with various (hetero)aryl bromides were employed in the triple relay process in good to excellent yields (85-99 %). Moreover, aryl methyl sulfoxides, dibenzyl sulfoxides, and dimethylsulfoxide could be utilized to generate diaryl sulfoxides involving multiple catalytic cycles by a single catalyst. Three for one: The [Pd(dba)2]/NiXantPhos (dba=dibenzylideneacetone) catalyst system successfully promotes a triple relay process involving sulfoxide α-arylation, C-S bond cleavage, and C-S bond formation to give diaryl sulfoxides (see picture). Aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides reacted with various (hetero)aryl bromides. Copyright
