50986-89-5Relevant academic research and scientific papers
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.
Catalyst-free visible-light-initiated oxidative coupling of aryldiazo sulfones with thiols leading to unsymmetrical sulfoxides in air
Liu, Qishun,Wang, Leilei,Yue, Huilan,Li, Jiang-Sheng,Luo, Zidan,Wei, Wei
supporting information, p. 1609 - 1613 (2019/04/08)
A facile and efficient visible-light-driven method has been developed to construct sulfoxides via oxidative coupling of aryldiazo sulfones with thiols using the O2 in air as the oxidant. This reaction could be performed at room temperature under catalyst- and additive-free conditions. The present methodology offers a mild and environmentally benign approach to obtain a library of sulfoxides in good yields with favorable functional group tolerance.
Method for preparing visible light promoted asymmetric sulfoxide compound
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Paragraph 0046; 0047, (2019/06/11)
The invention belongs to the field of organic synthetic chemistry, particularly relates to a preparation method of an asymmetric sulfoxide compound, and particularly discloses a method for synthesizing the asymmetric sulfoxide compound based on visible light catalysis. A compound shown in the formula I and a compound shown in the formula II are added to a reactor, a mixture of an organic solvent and water is added as a reaction solvent, the reactor is connected to air, under the irradiation of visible light, a reaction at a room temperature is performed for 16-40 hours; and after a detection reaction of a TLC thin layer chromatography plate is completed, pure water is added, then the extraction is performed, extract liquid is combined and dried, the extract liquid is concentrated and purified to obtain a compound shown in the formula III, and the compound is the asymmetric sulfoxide compound. The reaction conditions are mild, energy is clean, a strong oxidant is not needed, the safetyof the reaction is improved, the pollution caused by using a metal reagent is avoided, and the reaction cost is saved.
Transition-Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information, p. 7104 - 7106 (2018/11/23)
A transition-metal-free arylation of sulfenate anions generated from β-sulfinyl esters with diaryliodonium salts was developed. In this process, a new C-S bond is formed under mild reaction conditions providing a wide range of S,S-diaryl and S-alkyl S-aryl sulfoxides.
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
, 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.
, 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
Direct S-arylation of unactivated arylsulfoxides using [Pd(IPr*)(cin) Cl]
Izquierdo, Frédéric,Chartoire, Anthony,Nolan, Steven P.
, p. 2190 - 2193 (2013/10/22)
The direct S-arylation of unactivated arylsulfoxides catalyzed by [Pd(IPr*)(cin)Cl] is described. Several arylmethylsulfoxides were coupled to various aryl halides in moderate to good yields (17 examples, 34-85%). Scope, limitations, and reaction mechanis
No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides
Chun, Joong-Hyun,Morse, Cheryl L.,Chin, Frederick T.,Pike, Victor W.
, p. 2151 - 2153 (2013/03/14)
No-carrier-added [18F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [18F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[18F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel 18F-labeling synthons and PET radiotracers.
