- Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction
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This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
- Pan, Yi,Wang, Yang,Wang, Yi,Zhang, Feng
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- Method for synthesizing sulfone compounds under photocatalysis condition
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The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.
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Paragraph 0154-0158
(2021/03/31)
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- Hantzsch Ester as a Visible-Light Photoredox Catalyst for Transition-Metal-Free Coupling of Arylhalides and Arylsulfinates
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Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (HEH) has been utilized as a visible-light photoredox catalyst for the cross coupling of arylhalides and arylsulfinates without transition metal, sacrificial agent, and mediator. This method is compatible with various functional groups and provides diaryl sulfones in good to high yields. Mechanistic studies indicate that this reaction undergoes the stepwise light irradiation of HE?, single electron transfer (SET) in donor–acceptor complex (DAC) from *HE? to arylhalide, trapping of aryl radical with sulfinate, and SET oxidation of sulfone radical anion by HE. to sulfone by the DAC method.
- Zhu, Da-Liang,Wu, Qi,Li, Hai-Yan,Li, Hong-Xi,Lang, Jian-Ping
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supporting information
p. 3484 - 3488
(2020/03/05)
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- Method for preparing heterocyclic sulfone organic compounds
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The invention discloses a method for preparing heterocyclic sulfone organic compounds from heterocyclic aryl halogen and aryl sulfinate. The method comprises the following steps: 1, in an inert gas protection, according to the molar ratio of heterocyclic aryl halogen compounds, benzene sulfinate compound, inorganic alkali to HEH of 1:2:1.5:0.2, adding the reactants into a reaction container provided with a stirring device, then adding dimethyl sulfoxide, and carrying out stirring reaction for 24 hours at room temperature under blue LED irradiation, so as to obtain the heterocyclic sulfone organic compound. According to the invention, HEH is used as a catalyst for the first time under the condition of not adding any auxiliary transition metal catalyst and precious metal photosensitizer, anda series of cross-coupling reactions of heterocyclic aryl halogen and benzene sulfinate are realized. In addition, the whole process is green, efficient and easy to operate, and the method is excellent for synthesizing the heterocyclic sulfone organic compound.
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Paragraph 0018-0021
(2020/05/08)
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- Selective Functionalization of Aminoheterocycles by a Pyrylium Salt
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The functionalization of aminoheterocycles by using a pyrylium tetrafluoroborate reagent (Pyry-BF4) is presented. This reagent efficiently condenses with a great variety of heterocyclic amines and primes the C?N bond for nucleophilic aromatic substitution. More than 60 examples for the formation of C?O, C?N, C?S, or C?SO2R bonds are disclosed herein. In contrast to C?N activation through diazotization and polyalkylation, this method is characterized by its mild conditions and impressive functional-group tolerance. In addition to small-molecule derivatization, Pyry-BF4 allows the introduction of functional groups in a late-stage fashion to furnish highly functionalized structures.
- Moser, Daniel,Duan, Yaya,Wang, Feng,Ma, Yuanhong,O'Neill, Matthew J.,Cornella, Josep
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p. 11035 - 11039
(2018/07/31)
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- Metal-free catalyzed arylsulfonylation of chloroquinoline with sodium arylsulfinates under microwave irradiation
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An efficient protocol for the synthesis of 2-arylsulfonyl quinolines has been developed via a metal-free catalyzed cross-coupling reaction of chloroquinoline with sodium arylsulfinates in moderate-to-good yields under microwave irradiation. The reactions proceed with a wide range of substrates with good functional group tolerance.
- Li, Xi-Yong,Sun, Ya-Min,Yuan, Jin-Wei
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p. 295 - 303
(2018/05/03)
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- Green chemical synthesis of 2-benzenesulfonyl-pyridine and related derivatives
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A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and>99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.
- Trankle, William G.,Kopach, Michael E.
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p. 913 - 917
(2012/12/30)
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