- Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis
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An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.
- Cui, Wenwen,Jiang, Min,Lv, Jian,Song, Xiuyan,Sun, Kai,Xu, Guiyun,Yan, Qiuli,Yang, Daoshan
-
supporting information
p. 3663 - 3668
(2021/05/31)
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- Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
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We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
- Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
-
supporting information
p. 8338 - 8342
(2021/10/25)
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- Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
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Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
- Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
-
supporting information
p. 2152 - 2155
(2021/03/06)
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- Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol
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Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.
- Chen, Yi-Xuan,Wang, Zhu-Jun,Xiao, Jun-An,Chen, Kai,Xiang, Hao-Yue,Yang, Hua
-
supporting information
p. 6558 - 6562
(2021/08/23)
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- Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy
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DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (~1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.
- Lin, Bizhen,Lu, Weiwei,Chen, Zhen-Yu,Zhang, Yue,Duan, Yin-Zhe,Lu, Xiaojie,Yan, Ming,Zhang, Xue-Jing
-
supporting information
p. 7381 - 7385
(2021/10/12)
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- Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron
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The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.
- Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei
-
supporting information
(2021/11/04)
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- Base-Promoted Stereoselective Hydrogenation of Ynamides with Sulfonyl Hydrazide to Give Z-Enamides
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A base-mediated semihydrogenation of ynamides using p-toluenesulfonyl hydrazide as an inexpensive and easy-to-handle hydrogen donor is reported. This transition-metal-free protocol avoids overhydrogenation and reduction of other functional groups, generating the thermodynamically unfavorable Z-enamides exclusively.
- Chen, Yanhui,Cheng, Guolin,Tian, Qingyu,Wen, Si,Zhang, Yuqing,Zhao, Zemin
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p. 10407 - 10413
(2021/08/20)
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- Preparation method of substituted sulfinate
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The invention discloses a preparation method of substituted sulfinate, which comprises the following steps: by using substituted sulfonyl chloride as a raw material, carrying out hydrolysis reductionreaction on the substituted sulfonyl chloride in water in the presence of a reducing agent and an acid-binding agent to generate the corresponding substituted sulfinate. The method is a novel method which is easy to implement and suitable for industrial scale production and is used for preparing sulfinate and derivatives thereof. The method is simple in technological process, high in product purity and safe and environment-friendly, wherein the waste gas, solid and liquid are easy to treat.
- -
-
Paragraph 0023-0029
(2020/12/30)
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- Synthetic method of zinc p-toluenesulfinate
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The invention discloses a synthesis method of zinc p-toluenesulfinate. The method comprises the following steps: S1, reducing p-toluenesulfonyl chloride into p-toluenesulfinate in the presence of an inorganic base by using the p-toluenesulfonyl chloride as a starting raw material, sodium sulfite as a reducing agent and water as a solvent to obtain a p-toluenesulfinate aqueous solution; and S2, adding a zinc chloride aqueous solution into the p-toluenesulfinate aqueous solution obtained in the S1, and carrying out a reaction; and carrying out cooling, carrying out filtering, carrying out washing by using water and carrying out drying to obtain the target product zinc p-toluenesulfinate, wherein the reaction temperature in the S2 is 72-88 DEG C, and the reaction time is 60-120 min; and preferably, the reaction temperature in the S2 is 79-83 DEG C, and the reaction time is 80-100 min. The synthetic method disclosed by the invention has the advantages of safety, environmental protection, ahigh yield, simple operation, raw materials convenient and easy to obtain, and low price; and the method is a synthetic route suitable for industrial production.
- -
-
Paragraph 0038-0090
(2020/01/25)
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- Phenyl pyrrole compound and application thereof in bactericidal activity
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The invention provides a novel phenyl pyrrole compound, and the phenyl pyrrole compound shows good bactericidal activity and can be used for preparing a broad-spectrum plant bactericide. In addition,the synthesis route is simple, the operation is convenient, the synthesis cost is reduced, and ecological environment pollution to soil, surface water, underground water and the like is avoided.
- -
-
Paragraph 0137-0138
(2020/08/17)
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- Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro
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Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.
- Iqbal Choudhary, M.,Iqbal, Sarosh,Khan, Ajmal,Khan, Khalid Mohammed,Kiran, Shumaila,Nazir, Rashid,Perveen, Shahnaz
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p. 244 - 255
(2020/03/10)
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- Alkene: Versus alkyne reactivity in unactivated 1,6-enynes: Regio-And chemoselective radical cyclization with chalcogens under metal-And oxidant-free conditions
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Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio-And chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C-SO2, C-C, and C-Se under extremely mild conditions. Furthermore, we achieved regio-And chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.
- Kudale, Vishal Suresh,Li, Jing,Mutra, Mohana Reddy,Tsai, Wu-Hsun,Wang, Jeh-Jeng
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supporting information
p. 2288 - 2300
(2020/04/21)
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- (2-Fluoroallyl)palladium complexes as intermediates in Pd-catalyzed Tsuji-Trost 2-fluoroallylations: Synthesis and reactivity
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The first examples of π-(2-fluoroallyl)palladium complexes were synthesized, isolated and characterized including chloride dimers, neutral chloride or cationic triflate complexes bearing PPh3 or SPhos as the ligands. Preliminary reactivity patterns indicating strong dependence of the chemoselectivity on “hardness” of the nucleophile and the ligand type were studied.
- Bobrova, Angelina Yu.,Mezentsev, Igor A.,Novikov, Maxim A.,Tomilov, Yury V.
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-
- Synthesis method of substituted thiophenol (by machine translation)
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The invention provides a method for synthesizing substituted thiophenol, which comprises the following steps of preparing compound V compound and NaHSO3 Or KHHSO3 Reaction synthesis IV compound, compound of formula IV and SO2 Reaction-synthesis III compounds of formula III are passed NaBH in NaOH solution. 4 Of formula II is reduced and the compound of formula II is acidified to give a compound of formula I. The method for synthesizing the substituted thiophenol has the advantages of greenness, high efficiency, easiness in industrial application and the like. (by machine translation)
- -
-
Paragraph 0017; 0043; 0044
(2020/06/09)
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- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
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A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
-
supporting information
p. 6600 - 6604
(2020/09/02)
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- Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position
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An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection. This journal is
- Lv, Fan,Guo, Xing,Wu, Hao,Li, Heng,Tang, Bing,Yu, Changjiang,Hao, Erhong,Jiao, Lijuan
-
supporting information
p. 15577 - 15580
(2020/12/30)
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- Styrene sulfone NLRP3 inflammasome inhibitor, preparation method and application thereof
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The invention relates to the field of styrene sulfone compounds and NLRP3 inhibitors, and particularly provides a styrene sulfone NLRP3 inflammasome inhibitor, a preparation method and application thereof, wherein the inhibitor is represented by a formula (1), n is selected from 0 and 1, X is selected from N and O, R1 is selected from different electron withdrawing or electron donating substituents, and R2 is selected from different fat or aromatic substituents. According to the invention, it is verified that the compounds represented by the general formula have NLRP3 inhibitory activity.
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-
-
- Nitrogen-substituted phenyl pyrrole compound and application thereof in plant sterilization
-
The invention provides a novel nitrogen-substituted phenyl pyrrole compound. The phenyl pyrrole compound shows good bactericidal activity and can be used for preparing bactericides with high-selectivity sterilization. Moreover, the synthesis route is simple, the operation is convenient, the synthesis cost is reduced, and ecological environment pollution to soil, surface water, underground water and the like is avoided.
- -
-
Paragraph 0143; 0152-153
(2020/07/21)
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- Hypervalent Iodine Mediated Sulfonamide Synthesis
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A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.
- Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
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supporting information
p. 2695 - 2701
(2019/04/08)
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- Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
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Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
- Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
-
supporting information
p. 4179 - 4188
(2019/05/08)
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- Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis
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The anti-Markovnikov hydrosulfonylation of unactivated alkenes with sodium sulfinates was realized via [Ir(dF(CF3)ppy)2(dtbbpy)]PF6-mediated visible light photoredox catalysis. The presence of an acid such as acetic acid is essential for the reaction to take place. A variety of unactivated alkenes can be transformed into sulfones with good yield and high regioselectivity using this reaction, which is proposed to proceed by a radical mechanism.
- Wang, Juan-Juan,Yu, Wei
-
supporting information
p. 9236 - 9240
(2019/11/19)
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- A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides
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A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).
- Chen, Lei,Liang, Jie,Chen, Zhen-yu,Chen, Jie,Yan, Ming,Zhang, Xue-jing
-
supporting information
p. 956 - 960
(2019/01/25)
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- Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones
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Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper-catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.
- Gómez, José Enrique,Cristòfol, àlex,Kleij, Arjan W.
-
supporting information
p. 3903 - 3907
(2019/02/24)
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- Pd(II)-Catalyzed Direct Sulfonylation of Benzylamines Using Sodium Sulfinates
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A Pd(II)-catalyzed direct sulfonylation of benzylamines with sodium sulfinates using a removable bidentate directing group is illustrated. The transformation is highly regioselective and tolerates wide functional groups. The mechanistic study reveals that radical species are involved in this reaction. This method delivers a direct synthetic strategy to obtain highly functionalized sulfonylated benzylamines.
- Karmakar, Ujjwal,Samanta, Rajarshi
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p. 2850 - 2861
(2019/03/29)
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- Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C-C σ-Bonds in Cyclopropanes with iPrOH
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A new rhodium porphyrin catalyzed regioselective transfer hydrogenolysis of both activated and unactivated cyclopropanes employing iPrOH as the hydrogen source was discovered. The reaction mechanism for the C-C σ-bond activation of cyclopropanes was identified through an initial radical substitution with rhodium(II) metalloporphyrin radical to give a rhodium porphyrin alkyl, followed by hydrogenolysis with iPrOH to give the corresponding acyclic alkanes and regenerate rhodium(II) metalloporphyrin radical.
- Chen, Chen,Feng, Shiyu,Chan, Kin Shing
-
supporting information
p. 2582 - 2589
(2019/07/02)
-
- Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts
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Diarylfluoromethylsulfonium salts, alternatives to freons or advanced fluorinated building blocks, are bench stable and easy-to-use sources of direct fluoromethylene (:CHF) transfer to alkenes. These salts enabled development of a trans-selective monofluorinated Johnson-Corey-Chaykovsky reaction with vinyl sulfones or vinyl sulfonamides to access synthetically challenging monofluorocyclopropane scaffolds. The described method offers rapid access to monofluorinated cyclopropane building blocks with further functionalization opportunities to deliver more complex synthetic targets diastereoselectively.
- Melngaile, Renate,Sperga, Arturs,Baldridge, Kim K.,Veliks, Janis
-
supporting information
p. 7174 - 7178
(2019/09/12)
-
- Switchable regioselection of C-H thiolation of indoles using different TMS counterions
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A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
- Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
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p. 11864 - 11867
(2019/10/11)
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- Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates
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Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.
- Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui
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p. 13465 - 13472
(2019/10/16)
-
- Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters
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We describe here the first general asymmetric synthesis of sterically encumbered α,α-disubstituted allylic sulfones via Pd-catalyzed allylic substitution. The design and application of a new and highly efficient phosphoramidite ligand (L10) proved to be crucial, and a wide variety of challenging allylic sulfones featuring quaternary stereocenters could be obtained in good yields and with good to excellent levels of regio- and enantioselectivities under attractive process conditions. The developed methodology employs easily accessible chemical feedstock including racemic allylic precursors and sodium sulfinates. The utility of the method is further demonstrated by the synthesis of the sesquiterpene (?)-Agelasidine A.
- Cai, Aijie,Kleij, Arjan W.
-
supporting information
p. 14944 - 14949
(2019/11/05)
-
- Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
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A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.
- Liu, Saiwen,Chen, Ru,Zhang, Jin
-
-
- Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions
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An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.
- Liu, Yanan,Xie, Peizhong,Sun, Zuolian,Wo, Xiangyang,Gao, Cuiqing,Fu, Weishan,Loh, Teck-Peng
-
supporting information
p. 5353 - 5356
(2018/09/13)
-
- Design, synthesis and biological evaluation of novel 2-sulfonylindoles as potential anti-inflammatory therapeutic agents for treatment of acute lung injury
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Acute lung injury (ALI) is primarily driven by inflammation that severely impacts lung function. Novel 2-sulfonylindoles were recently shown to exhibit anti-inflammatory activity through the inhibition of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) production. Here, we synthesized 31 compounds which contained 2-sulfonylindole structure. The compounds 8a, 9g, 9h and 9k exhibited dose-dependent anti-inflammatory activity in vitro. Structural-activity relationship analysis revealed that the introduction of sulfonyl group in indole nucleus may be successful to obtain new anti-inflammatory structures and leads. The compounds 9h and 9k also decreased liposaccharide (LPS)-induced IL-6, IL-1β and vascular cell adhesion molecule-1 (VCAM-1) mRNA expression, both in vitro and in an in vivo model of ALI. Furthermore, the compounds 9h and 9k at a high dose (20 mg/kg) significantly protected against LPS-induced ALI in mice. These results show that compounds 9h and 9k could be a promising lead structure for the treatment of ALI.
- Xia, Qinqin,Bao, Xiaodong,Sun, Chuchu,Wu, Di,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Zhou, Jianmin,Liang, Guang
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p. 120 - 132
(2018/10/21)
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- Fe-based metal-organic frameworks for the synthesis of N-arylsulfonamides via the reactions of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes in water
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A newly developed chemoselective reaction of sodium arylsulfinates or arylsulfonyl chlorides with nitroarenes has been disclosed. The chemistry, in which non-toxic water and recyclable iron-based metal-organic frameworks are employed as the solvent and catalyst, respectively, provides an efficient approach for the generation of N-arylsulfonamides, which are widely present in biologically active compounds and drugs, rendering this methodology attractive to both synthetic and medicinal chemistry.
- Li, Xinxin,Chen, Fei,Lu, Guo-Ping
-
supporting information
p. 4226 - 4230
(2018/10/26)
-
- Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates
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A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well.
- Wang, Tianlei,Wang, Fumin,Shen, Jinghua,Pang, Tianting,Ren, Yanfei,Wu, Botao,Zhang, Xubin
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p. 1183 - 1187
(2018/02/26)
-
- Generation of trifluoromethyl thiolsulphonate through one-pot reaction of sulfonyl chloride and trifluoromethanesulfanylamides
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A novel and efficient tandem reaction of sulfonyl chloride and trifluoromethylsulfanylamide is described here for the synthesis of various trifluoromethyl thiolsulphonates with a broad functional group tolerance. In the process, it is believed that sulfinate generated from sulfonyl chloride is a critical intermediate and the additive 4-methylbenzenesulfonic acid (p-TsOH) facilitates the formation of “CF3S+”. Electrophilic trifluoromethylthiolation of in situ generated sulfinate and “CF3S+” provides the final products.
- Li, Yuewen,Qiu, Guanyinsheng,Wang, Hailong,Sheng, Jie
-
supporting information
p. 690 - 693
(2017/01/28)
-
- Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
-
A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
- Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
-
supporting information
p. 2056 - 2059
(2017/02/15)
-
- Methyl p-tolyl sulfone and preparation method
-
The invention discloses methyl p-tolyl sulfone and a preparation method. Methyl p-tolyl sulfone is prepared from components of raw and auxiliary materials in parts by weight as follows: 200 parts of water, 29 parts of sodium carbonate, 33 parts of anhydrous sodium sulfite, 45 parts of paratoluensulfonyl chloride, 1 part of activated carbon, 3 parts of sodium hydroxide and 16 parts of chloromethane. The preparation method comprises steps as follows: a) water is added to a salt formation kettle in proportion, stirring is started, sodium carbonate, anhydrous sodium sulfite and paratoluensulfonyl chloride are added once in proportion after heating, and the materials naturally react after a manhole is tightly closed; b) steam is introduced, heating and thermal insulation are performed, and a paratoluensulfonyl chloride solution is prepared; c) activated carbon is added in proportion during stirring, hot filtration is performed during stirring, and the mixture is subjected to direct replacement and then enters a methylation reaction kettle; d) steam is introduced, heating is performed, a chloromethane pipeline valve is opened for a methylation reaction; a methylation reduction reaction is performed again after thermal insulation; e) sodium hydroxide is sucked once for a neutralization reaction; f) the mixture is transferred into a centrifugal machine to be spin-dried and then transferred into an oven to be dried.
- -
-
Paragraph 0043; 0044; 0049; 0050; 0051; 0056; 0057
(2017/04/03)
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- Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
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A highly efficient iodine/TBHP-mediated one-pot deoxygenative and regioselective 2-sulfonylation of quinoline N-oxides with sodium sulfinate salts has been developed. This metal-, base-, and phosphorus-free protocol employs readily accessible and easy-to-handle reagents and can be conveniently carried out at room temperature under mild conditions, providing an alternative access to a series of 2-sulfonylquinolines and other related heteroaryl sulfone products in moderate-to-excellent yields within a short reaction time.
- Sumunnee, Ladawan,Buathongjan, Chonchanok,Pimpasri, Chaleena,Yotphan, Sirilata
-
supporting information
p. 1025 - 1032
(2017/02/15)
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- Rhodium-catalyzed odorless synthesis of diaryl sulfides from borylarenes and: S -aryl thiosulfonates
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Various diaryl sulfides, including heteroaryl- and nitrogen-containing sulfides, have been efficiently prepared by rhodium-catalyzed odorless deborylative arylthiolation of organoborons with S-aryl thiosulfonates. The ready availability of starting materials and further transformation of sulfides have rendered a diverse range of organosulfur compounds easily accessible.
- Kanemoto, Kazuya,Sugimura, Yasuyuki,Shimizu, Shigeomi,Yoshida, Suguru,Hosoya, Takamitsu
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supporting information
p. 10640 - 10643
(2017/10/06)
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- Preparation method of aromatic sulfinic acid compound
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The invention relates to a preparation method of an aromatic sulfinic acid compound. The preparation method includes the steps of: with Lewis acid as a catalyst, performing a Friedel-Crafts acylation reaction to an aromatic compound as a raw material with 1,4-diazabicyclo[2.2.2]octane (DABSO) in a solvent to generate a corresponding aromatic sulfinic acid compound. Compared with industrial preparation methods for the aromatic sulfinic acid compound in the prior art, the method can synthesize the aromatic sulfinic acid compound in one step, so that experiment operations are simplified and a high-polluting chlorosulfonation step is avoided. The method has mild reaction conditions, wherein the reaction can be carried out under a common normal temperature condition, so that a large amount of energy consumption in production is reduced. The DABSO, compared with gas-phase SO2, is convenient to store and transport, has stable properties at normal temperature and under normal pressure and has safe and simple operations. The raw materials are low in cost and easy to obtain, thus reducing production cost. The method has huge potential in practical use.
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Paragraph 0026; 0027; 0028; 0029; 0030
(2017/09/26)
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- Copper-Mediated 1,2-Difunctionalization of Styrenes with Sodium Arylsulfinates and tert-Butyl Nitrite: Facile Access to α-Sulfonylethanone Oximes
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A new copper-mediated synthesis of α-sulfonylethanone oximes from styrenes, sodium arylsulfinates and tert-butyl nitrite (t-BuONO; TBN) is presented. This intermolecular three-component method enables the one-step formation of C N and C S bonds under mild conditions, and represents a new, straightforward approach to α-sulfonylethanone oximes. (Figure presented.) .
- Yang, Ji,Liu, Yan-Yun,Song, Ren-Jie,Peng, Zhi-Hong,Li, Jin-Heng
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supporting information
p. 2286 - 2292
(2016/07/28)
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- Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate
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An unexpected Cu-catalyzed deoxygenative C2-sulfonylation reaction of quinoline N-oxides in the presence of radical initiator K2S2O8 was developed that used sodium sulfinate as a sulfonyl coupling partner. The mechanism studies indicate that the reaction proceeds via Minisci-like radical coupling step to give sulfonylated quinoline with good chemical yields.
- Du, Bingnan,Qian, Ping,Wang, Yang,Mei, Haibo,Han, Jianlin,Pan, Yi
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supporting information
p. 4144 - 4147
(2016/08/30)
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- Synthetic method of 4-methylsulfonyl methylbenzene
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The invention discloses a synthetic method of 4-methylsulfonyl methylbenzene. The method comprises the following steps in sequence: by taking 4-toluene sulfonyl chloride as a start material, feeding through fusion, performing a reduction reaction between the 4-toluene sulfonyl chloride and sodium sulfite in an alkali aqueous solution so as to generate sodium 4-methyl benzene sulfinate; performing a methylation reaction between the sodium 4-methyl benzene sulfinate and chloromethane, enabling a reaction product to be subjected to the post treatment such as filtration and recrystallization to obtain the product 4-methylsulfonyl methylbenzene. According to the invention, chlorosulfonyl is converted into methylsulfonyl in a one-pot manner; production equipment and technological operation are simplified, the loss brought about by material transfer is reduced, and the product yield is improved.
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Paragraph 0056; 0057; 0058
(2016/11/24)
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- Iron-catalyzed synthesis of arylsulfinates through radical coupling reaction
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A novel strategy for installation of a sulfonyl fragment into arenes has been accomplished via an iron-catalyzed radical coupling reaction. Arene radicals derived from diaryliodoniums via single electron transfer reaction combine with sulfoxylate anion radicals readily generated from commercially available rongalite (HOCH2SO2Na·2H2O) to afford arylsulfinates efficiently at room temperature. In this protocol, a broad range of functional groups are tolerated to give products in good yields.
- Zhang, Weixi,Luo, Meiming
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supporting information
p. 2980 - 2983
(2016/02/19)
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- Method for preparing aryl sulfinate
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The invention provides a method for preparing an aryl sulfinate compound through the reaction of diaryl iodonium salt and sodium formaldehyde sulfoxylate.At room temperature, the diaryl iodonium salt reacts with the sodium formaldehyde sulfoxylate for 10-120 minutes to generate the corresponding aryl sulfinate compound.The method has the advantages that the reaction conditions are mild, the used reagents re easy to obtain, the application range of a substrate is wide, operation is simple, reaction is quick, and the like.
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Paragraph 0016
(2016/10/08)
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- Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
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Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.
- Meyer, Andreas Uwe,J?ger, Stefanie,Prasad Hari, Durga,K?nig, Burkhard
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supporting information
p. 2050 - 2054
(2015/06/23)
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- Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides
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Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright
- Liu, Jidan,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Yang, Zhiyong,Tan, Ze
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supporting information
p. 3196 - 3202
(2014/06/09)
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- Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies
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A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).
- Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats
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p. 12018 - 12032
(2015/01/16)
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- Copper-catalysed coupling of aryl tosylates with sodium arylsulfinates
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Diaryl sulfones derivatives were easily synthesised from aryl tosylates and sodium arylsulfinates in high yields using [Cu(CH3CN)4]PF6 as catalyst. The transformation is efficient, simple and the starting materials are readily available.
- Wang, Chunjie,Zhang, Hui,Li, Zhiwei,Wang, Ziyun
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p. 639 - 642
(2015/02/02)
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- First palladium-catalyzed denitrated coupling of nitroarenes with sulfinates
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The first example of palladium-catalyzed protocol for the denitrated coupling of nitroarenes with sulfinates was developed, achieving aryl and heterocyclic sulfones in moderate to excellent yields. The cyclopalladated ferrocenylimine (I) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol %). The efficiency of this reaction was demonstrated by compatibility with a wide range of groups. Thus, the method represents a simple and facile procedure to access aryl and heterocyclic sulfones.
- Tian, Heng,Cao, Aijuan,Qiao, Lijun,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
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supporting information
p. 9107 - 9112
(2015/03/05)
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