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Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides
A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent N-S bond ary
Du, Xian,Li, Yihui,Luo, Yong,Xu, Dejing,Xu, Xiaohong,Xue, Can,Yuan, Han,Zhen, Jingsong
p. 1986 - 1991
(2022/02/07)

Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones
A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated. This journal is
Feng, Yueji,Tuo, Yanyan,Zhang, Xiaohui,Zheng, Qing-Zhong
supporting information
p. 768 - 772
(2022/02/03)

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling
An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.
Adenot, Aurélien,Anthore-Dalion, Lucile,Nicolas, Emmanuel,Berthet, Jean-Claude,Thuéry, Pierre,Cantat, Thibault
supporting information
p. 18047 - 18053
(2021/11/16)

On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle
A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.
Ge, Xin,Lei, Qiuyun,Liao, Xiong,Liu, Xuemin,Song, Weili,Wu, Lei,Wu, Siyuan,Zhou, Shaodong
(2021/09/15)

Sulfonylation of Bismuth Reagents with Sulfinates or SO2through BiIII/BiV Intermediates
Studies to explore the catalytic activities of main-group elements are attractive. We report here our study of sulfonylation of bismuth reagents with sulfinates or SO2 surrogates. Under oxidative conditions, triarylbismuthines and sulfinates were transformed into diaryl sulfones. A transition-metal-like two-electron redox process at the Bi center was achieved in this reaction. Sulfur dioxide generated in situ can also replace sulfinates to deliver the corresponding symmetric diaryl sulfones. A rational mechanism for this reaction was also proposed that involves a Bi(III)-Bi(V) manifold.
Zhao, Fengqian,Wu, Xiao-Feng
supporting information
p. 2400 - 2404
(2021/07/28)

Method for synthesizing sulfone compounds under photocatalysis condition
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 0105-0109

(2021/03/31)

Pd/NHC-catalyzed arylsulfonylation of boronic acids: A general and direct protocol to access diarylsulfones
For the first time, robust NHC-Pd complexes have been demonstrated as highly efficient catalysts in the direct arylsulfonylation of boronic acids. Remarkably, a broad number of diaryliodonium salts as powerful electrophilic arylation reagents are well compatible to form functional ortho-substituted diarylsulfones in satisfactory yields. Owing to the stronger σ-donor and weaker π-acceptor properties, the acenaphthoimidazolylidene ligands exhibit higher catalytic activities towards this challenging one-step arylsulfonylation reaction.
Zhu, Haibo,Yang, Liu,Meng, Jia,Xie, Zongbo,Le, Zhang-Gao,Tu, Tao
supporting information

(2020/12/29)

Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water
A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.
Ge, Xin,He, Xi,Liu, Xuemin,Qian, Chao,Song, Weili,Yang, Jinguo,Zhou, Shaodong
supporting information
p. 6322 - 6329
(2021/09/10)

Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
p. 2447 - 2458
(2020/04/15)

Micelle catalysis and extraction separation coupling method based on nonionic surfactant (by machine translation)
The invention discloses a micelle catalysis and extraction separation coupling method based on a nonionic surfactant, and belongs to the technical field of chemical synthesis. M 202070 is used as a reaction medium, the Ullmann C-S coupling reaction is catalyzed, and the product is separated by directly heating to a cloud point after the reaction is completed. The method provided by the invention is mild in condition, convenient to operate, less in organic matter content in the reaction waste liquid, small in environmental pollution, green and environment-friendly; meanwhile, the yield of the aromatic sulfone can reach 75% or above, the extraction yield reaches 100%, and the method is suitable for industrial mass production. (by machine translation)
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Paragraph 0057-0061

(2020/08/18)

Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions
The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.
Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min
supporting information
p. 433 - 438
(2020/02/13)

Oxidation of aromatic sulfides with molecular oxygen: Controllable synthesis of sulfoxides or sulfones
The recent development of selective oxidation of aromatic sulfides with molecular oxygen was highlighted. The sulfoxides and sulfones could be obtained by simply switching the reaction media, i.e., bis(2-butoxyethyl)ether (BBE) or poly(ethylene glycol)dimethyl ether (PEGDME). The application of the high-boiling-point polyether as an initiator and green media can eliminate the need of large quantities of additives and volatile solvents. This strategy represents an economic and eco-friendly method that could find potential applications.
Tang, Lili,Du, Kejie,Yu, Bing,He, Liangnian
p. 2991 - 2992
(2020/03/24)

Regiospecific Cleavage of S-N Bonds in Sulfonyl Azides: Sulfonyl Donors
Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various inactivated arenes to prepare sulfones at ambient temperature.
Zhang, Zhiguo,Wang, Songnan,Zhang, Yong,Zhang, Guisheng
p. 3919 - 3926
(2019/03/29)

Synthesis method of diaryl sulfone compound (by machine translation)
The invention discloses a synthesis method of a diaryl sulfone compound, wherein the, reaction equation of the series of N - diarylsulfone compounds is prepared by (NFSI) sulfonylating the aromatic hydrocarbon under the non-metal condition with the source of the, benzenesulfonyl group as the benzenesulfonyl group, and: the reaction equation is as follows. STR3, #, STR2, #, STR2, #, #, #, # STR2. # STR2# STR2# STR2, , STR2 STR2 STR2 N - # (NFSI) STR2# STR2 STR2 STR2, #, # STR1 STR8# STR2 STR1 STR8. AlCl R3 , FeCl3 The other precious, and metals of, other metals such as the precious metals of, the other noble metals not cause the environment, to pollute, the environment and are suitable for the concise and high-efficiency synthesis of. the diarylsulfone compounds, and have good application prospects in the fields of organic synthesis, drug research and development and the like. (by machine translation)
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Paragraph 0007; 0017-0019

(2019/12/31)

Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO
We report a redox-neutral Ni(II)-catalyzed sulfination of readily available aryl and heteroaryl boronic acids. Using the combination of commercially available, air-stable NiBr2·(glyme), a commercially available phenanthroline ligand, and DABSO, boronic acids are efficiently converted to the corresponding sulfinate salts, which can be further elaborated to valuable sulfonyl-containing groups, including sulfones, sulfonamides, sulfonyl fluorides, and sulfonate esters. The catalyst loading can be reduced to 2.5 mol ?% on a gram scale. This practically simple protocol tolerates an unprecedented range of pharmaceutically relevant and electron-poor (hetero)aryl boronic acids, allowing the direct synthesis of active pharmaceutical ingredients.
Lo, Pui Kin Tony,Chen, Yiding,Willis, Michael C.
p. 10668 - 10673
(2019/11/11)

A designed bi-functional sugar-based surfactant: Micellar catalysis for C-X coupling reaction in water
A bi-functional sugar-based surfactant ALA14 was designed as the ligand and micelle constructor and demonstrated to promote the copper-catalyzed C-X coupling reaction in water. The nature of this micelle, formed by sugar-based surfactants, was investigated with CMC, DLS, and TEM, by which encapsulation and aggregation of the substrates in micelles were verified. Additionally, it was addressed by 1H-NMR analysis that the enrichment position of the substrates is in the lipophilic alkyl chain. Finally, moderate to excellent yields of the aimed products were obtained in this work. This remarkably simple strategy expanded the scope of C-X coupling reaction in water; most notably, both water and ALA14 can be recycled and reused.
Ge, Xin,Zhang, Shihui,Chen, Xinzhi,Liu, Xuemin,Qian, Chao
supporting information
p. 2771 - 2776
(2019/06/13)

Method for photocatalytic synthesis of sulfur sulfone compounds
The invention discloses a method for photocatalytic synthesis of sulfur sulfone compounds, and belongs to the technical field of catalysis. The invention provides a novel green environmentally-friendly method to efficiently synthesize the sulfur sulfone derivatives, and one thioether compound and an oxidizing agent are subjected to direct oxidization to form one corresponding sulfur sulfone compound under illumination by utilizing cercosporin as a catalyst. The method provided by the invention adopts the cercosporin as the catalyst, the catalytic conditions are milder, the reaction can be performed at room temperature under visible light irradiation, the catalyst has high catalytic activity and can be used for high-selectivity catalytic synthesis of the sulfur sulfone compounds, and the micro catalyst can make a yield higher, wherein the yield can reach 90% or more; and the photocatalyst and substrate raw materials used in the method are simple and easy to obtain, have low costs and can be produced on a large scale, and the method has very good application prospects.
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Paragraph 0046-0047

(2019/05/15)

Method for preparing aryl sulfone compound as well as method for extracting catalyst and aryl sulfone compound
The invention provides a preparation method of an aryl sulfone compound, which is characterized in that in an organic solvent and under an aerobic atmosphere, a catalytic system composed of a metal-ligand-TEMPO is used for catalytic oxidation of a thioether compound to obtain the aryl sulfone compound. The preparation method is simple, green, and efficient, the reaction condition is mild, and theapplication range is wide; the invention also provides a method for extracting a catalyst and the product aryl sulfone compound used in the preparation process. The ethyl acetate is added to a reaction mixture, steps of filtering and condensation under reduced pressure are carried out to obtain a filtrate and the catalyst, and silica gel column chromatography and concentration extraction are carried out to obtain the aryl sulfone compound. The extraction method is simple, and the extracted catalyst has high activity and good cycle stability, and the extraction rate of the product aryl sulfonecompound is high.
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Paragraph 0064-0067

(2019/02/13)

Copper-mediated sulfonylation of aryl iodides and bromides with arylsulfonyl hydrazides in PEG-400
Sulfonylation using stable and readily available arylsulfonyl hydrazides and aryl iodides or bromides mediated by cupric acetate has been achieved. Using polyethylene glycol (PEG-400) as an eco-friendly medium, the coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields without the presence of additional ligands and base.
Wu, Xiangmei,Wang, Yan
supporting information
p. 10953 - 10957
(2018/07/06)

Efficient Ullmann C-X coupling reaction catalyzed by a recoverable functionalized-chitosan supported copper complex
Three different types of functionalized-CS were prepared and anchored with copper salts for use as the catalyst for the Ullmann C-X coupling reaction. The Schiff-basic chitosan supported copper complex (PCCS@CuI) exhibits the highest catalytic activity. The structure of the catalyst was characterized by FTIR spectroscopy, TG, XRD, SEM, EDS and XPS. This catalyst exhibited high applicability for the C-N and C-S coupling reactions, in which good to excellent yields were obtained. Its easy separation, good reusability and stability were notable.
Liu, Xuemin,Chang, Shuo,Chen, Xinzhi,Ge, Xin,Qian, Chao
supporting information
p. 16013 - 16020
(2018/10/04)

Mechanistic aspects of copper (II)-catalyzed synthesis of sulfones from sulfinate salts and aryl halides under C-S coupling
Copper(II)-catalyzed synthesis of sulfones from sulfinate salts and aryl halides was investigated by means of a combination of experiment and DFT calculation. Experimental results demonstrated the wide applicability of the title approach. The reaction mechanisms are revealed by in-situ IR and theoretical study. It reveals remarkable ligand effect the bidentate amine plays in the reaction, that is, it initially activats the C-I bond of iodobenzene so as to enhance the whole catalytic process.
Ge, Xin,Sun, Fengli,Liu, Xuemin,Chen, Xinzhi,Qian, Chao,Zhou, Shaodong
p. 72 - 78
(2018/04/26)

The highly selective metal-free oxidation of sulfides, tellurides and phosphines using sodium bromate in the presence of recyclable ionic liquid [bmim]HSO4, at 80°C
The metal-free oxidation of sulfides to sulfones using sodium bromate (NaBrO3) in [bmim]HSO4:H2O (3:1, v/v) at 80°C is reported. Phenylalkyl, phenylbenzyl, diaryl and heteroaryl sulfides were transformed to the corresponding sulfones. Aryl tellurides and phosphines were oxidised to the corresponding telluroxides and phosphine oxides. All the reactions proceeded smoothly and gave high yields in 20-55 min. The ionic liquid [bmim]HSO4 was easily recovered and recycled.
Rajeswari,Lumb, Anshika,Khurana, Jitender M.
p. 442 - 444
(2016/07/21)

One-pot synthesis of aryl sulfones from organometallic reagents and iodonium salts
A transition-metal-free arylation of lithium, magnesium, and zinc sulfinates with diaryliodonium salts is described. The sulfinic acid salts were prepared from the reaction of the corresponding organometallic reagents and sulfur dioxide. Combination of the three single steps (preparation of the organometallic compound, sulfinate formation, and arylation) leads to a one-pot sequence for the synthesis of aryl sulfones from simple starting materials. The chemoselectivity of unsymmetrical diaryliodonium salts has been investigated. Potential and limitations of this method will be discussed.
Margraf, Natalie,Manolikakes, Georg
p. 2582 - 2600
(2015/03/18)

The synthesis of diarylsulfones with simple arenes and K2S2O8 through double C-S bond formation
An unprecedented double C-S bond formation method has been developed to prepare both symmetric and unsymmetric diarylsulfones with simple arenes in a single step. This represents the first example that K2S2O8 can be employed as a highly effective sulfonating agent to synthesize diarylsulfones. The reaction demonstrates excellent reactivity, good functional group tolerance and high yields.
Yang, Yiqing,Chen, Zhang,Rao, Yu
supporting information
p. 15037 - 15040
(2014/12/11)

D-Glucosamine as a green ligand for copper catalyzed synthesis of aryl sulfones from aryl halides and sodium sulfinates
d-Glucosamine is reported for the first time as a green ligand for copper catalyzed coupling of aryl halides and sodium sulfinates, which provides a simple and extremely efficient new route to unsymmetrical diaryl sulfones. The catalytic reaction proceeded in DMSO-H2O at 100°C and gave a variety of aryl sulfones in high yields. The high water solubility of the ligand enables easy catalyst removal. The scope of the method was validated by a single step synthesis of marketed drug zolimidine, a drug used for peptic ulcers, in 65% yield.
Yang, Ming,Shen, Hongyun,Li, Yuanyuan,Shen, Chao,Zhang, Pengfei
p. 26295 - 26300
(2014/07/08)

A mild and base-free synthesis of unsymmetrical diaryl sulfones from arylboronic acids and arylsulfonyl hydrazides
A mild and efficient synthesis of diaryl sulfones from arylboronic acids and arylsulfonyl hydrazides is described. Promoted by cupric acetate and in the absence of additional ligand and base, the cross-coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields at room temperature under neutral and ambient conditions. Georg Thieme Verlag Stuttgart New York.
Wu, Xiang-Mei,Wang, Yan
supporting information
p. 1163 - 1167
(2014/05/20)

A highly active and easily recoverable chitosan@copper catalyst for the C-S coupling and its application in the synthesis of zolimidine
Aryl sulfones were synthesized using a highly active and easily recoverable heterogeneous Cu catalyst which was prepared by simply stirring an aqueous suspension of chitosan in water with copper salts. The chitosan@copper catalyst catalyzed the coupling reactions of aryl halides with sodium sulfinates to readily give the corresponding sulfones in good to excellent yields. The highly active catalyst can be reused many times without losing its catalytic activity. In addition, by using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily. This journal is the Partner Organisations 2014.
Shen, Chao,Xu, Jun,Yu, Wenbo,Zhang, Pengfei
supporting information
p. 3007 - 3012
(2014/06/10)

Diaryl sulfones synthesis with aryltrifluoroborates and aryl sulfinic salts under mild conditions
CuI-catalysed cross-coupling reactions of various aryltrifluoroborates with aryl sulfinic salts have been achieved in good yields. A new efficient method is described for the conversion of potassium aryltrifluoroborates into diaryl sulfones. The reported reactions are tolerant to common functional groups regardless of whether they are electron-rich or electron-deficient, making this transformation an attractive alternative to traditional approaches.
Zhang, Wei,Li, Ke,Zhao, Baoli
p. 269 - 271
(2014/06/09)

Copper-mediated cascade synthesis of diaryl sulfones via the sandmeyer reaction
A convenient and efficient method for the copper-mediated cascade synthesis of diaryl sulfones via the Sandmeyer reaction has been developed. The protocol uses readily available aryl amines and arylsulfinic acids as the starting materials, isoamyl nitrite as the diazotizating reagent of the aryl amines, and the method shows mild reaction conditions and high tolerance towards various functional groups in the substrates. Georg Thieme Verlag Stuttgart New York.
Yang, Xiaobo,Shi, Liangliang,Fu, Hua
p. 847 - 852
(2014/04/17)

Arylation of lithium sulfinates with diaryliodonium salts: A direct and versatile access to arylsulfones
An efficient, transition-metal-free arylation of lithium sulfinates, which are readily accessible from reactions of organolithium reagents with sulfur dioxide, is described. Based on this method, a practical protocol for the direct transformation of (hetero)arenes and (hetero)aromatic halides into diarylsulfones was developed.
Umierski, Natalie,Manolikakes, Georg
p. 4972 - 4975
(2013/10/22)

A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones
An efficient and general protocol for the synthesis of diaryl sulfones via the metal-free coupling of readily available diaryliodonium salts and arenesulfinates in PEG-400 under microwave irradiation has been developed. Utilizing this metal-free and eco-friendly protocol, we have prepared various diaryl sulfones in high yields and shorter reaction times under mild conditions. Furthermore, the coupling of diaryliodonium with arenesulfinate salts with and without copper iodide provides a convenient access to various diaryl sulfones with high selectivity. Georg Thieme Verlag Stuttgart · New York.
Kumar, Dalip,Arun,Pilania, Meenakshi,Shekar, K.P. Chandra
p. 831 - 836
(2013/06/05)

Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts
An efficient, high-yielding, and transition-metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts has been developed. The mild reaction conditions tolerate a range of functional groups, and unsymmetrical diaryliodonium salts show high chemoselectivity.
Umierski, Natalie,Manolikakes, Georg
supporting information
p. 188 - 191
(2013/03/28)

PROCESS FOR THE PRODUCTION OF A SULFONE MONOMER
The present invention provides an economic and environmentally friendly method for the preparation of polymer grade 4,4'-dichlorodiphenyl sulfone which is substantially free of 2,4' and 3,4'-isomers of dichlorodiphenyl sulfone with yield of over 90%, with substantially reduced reaction times without the use of impregnated catalysts. Further no toxic byproducts such as dimethyl pyrosulfate are formed thereby reducing the load on effluent treatment with the added advantage of substantially recycling the reactants and byproducts. Further the present invention discloses a process is disclosed in which isomeric mixture of 4,4'-, 3,4'-, and 2,4'-dichlorodiphenyl sulfone produced during the preparation of 4,4'-dichlorodiphenyl sulfone is converted to value added products such as diphenyl sulfone, 2,4'- dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfone and 2-aminodiphenyl sulfone.
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(2011/06/25)

Sulfonylation of aromatic compounds with sulfonic acids using silica gel-supported AlCl3 as a heterogeneous Lewis acid catalyst
Silica gel-supported aluminum chloride (SiO2-AlCl3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The catalyst can be prepared easily with cheap starting materials and is stable (as a bench-top catalyst) and reusable.
Parvanak Boroujeni, Kaveh
experimental part
p. 197 - 203
(2010/11/05)

Polystyrene supported Al(OTf)3: A stable, efficient, selective, and reusable catalyst for sulfonylation of arenes with sulfonic acids
Cross-linked polystyrene supported aluminium triflate (Ps-Al(OTf) 3) was found to be an efficient and chemoselective heterogeneous Lewis acid catalyst for the direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The solid acid catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency.
Boroujeni, Kaveh Parvanak
experimental part
p. 1887 - 1890
(2010/11/18)

Inhibitors of the salicylate synthase (Mbti) from Mycobacterium tuberculosis discovered by high-throughput screening
A simple steady-state kinetic high-throughput assay was developed for the salicylate synthase MbtI from Mycobacterium tuberculosis, which catalyzes the first committed step of mycobactin biosynthesis. The mycobactins are small-molecule iron chelators produced by M. tuberculosis, and their biosynthesis has been identified as a promising target for the development of new antitubercular agents. The assay was miniaturized to a 384-well plate format and high-throughput screening was performed at the National Screening Laboratory for the Regional Centers of Excellence in Biodefense and Emerging Infectious Diseases (NSRB). Three classes of compounds were identified comprising the benzisothiazolones (class I), diarylsulfones (class II), and benzimidazole-2-thiones (class III). Each of these compound series was further pursued to investigate their biochemical mechanism and structure-activity relationships. Benzimidazole-2-thione 4 emerged as the most promising inhibitor owing to its potent reversible inhibition.
Vasan, Mahalakshmi,Neres, Joao,Williams, Jessica,Wilson, Daniel J.,Teitelbaum, Aaron M.,Remmel, Rory P.,Aldrich, Courtney C.
experimental part
p. 2079 - 2087
(2011/11/29)

Aqueous sodium hypochlorite mediated chemoselective oxidation of chalcogenides to monoxides and dioxides by microwave exposure
A solvent-free, rapid, and highly selective oxidation of sulfides, selenides, and tellurides (chalcogenides) to the corresponding monoxides (sulfoxides, selenoxides, and telluroxides) or the corresponding dioxides (sulfones, selenones, and tellurones) has been developed using aqueous sodium hypochlorite on solid supports by exposure to microwave. Chemoselectivity and quantitative yields have been attained in most cases.
Khurana, Jitender,Nand, Bhaskara
experimental part
p. 906 - 909
(2011/01/08)

Flow-vacuum pyrolysis of polycyclic compounds. 251. Pyrolysis of some 3-mercapto-5-substituted-1,2,4-triazoles
The flow-vacuum pyrolysis (FVP) of the 3-mercapto-5-substituted-1,2,4- triazoles 5a-c, between 475°C - 750°C, at 2 mm Hg, in inert atmosphere (4mL/min argon flow rate) and quartz pyrolysis tube (60 cm length, 1 cm internal diameter, quartz chips filling 30 mm long) afforded a complex mixture with cyano-diphenyl-sulphones 12a-c and corresponding diphenylsulphones 13a-c as main products. The reaction products were identified by GC/MS. A radical mechanism is suggested in order to explain the formation of the main reaction products.
Istrati, Daniela,Popescu, Angela,Mihaiescu, Dan,Saramet, Ioana,Bala?u, Mihaela C.
experimental part
p. 497 - 503
(2009/05/11)

Highly selective catalytic Friedel-Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid
Friedel-Crafts sulfonylation of aromatic compounds was carried out using FeCl3-based ionic liquid. These liquids serve as efficient media as well as Lewis acid catalyst.
Bahrami, Kiumars,Khodei, Mohammad Mehdi,Shahbazi, Fomeida
p. 3931 - 3934
(2008/09/21)

A practical and efficient method for the preparation of aromatic sulfones by the reaction of aryl sulfonyl chlorides with arenes catalysed by Fe(OH) 3
Fe (OH)3 catalyses Friedel-Crafts sulfonylation of arenes with aryl sulfonyl chlorides to obtain the corresponding diaryl sulfones in good yields.
Jin, Tongshou,Zhao, Ying,Ma, Yanran,Li, Tongshuang
p. 2183 - 2185
(2007/10/03)

A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts
A new efficient and mild preparation of sulfones from boronic acids and sulfinic acid salts is reported. The cross-coupling reaction mediated by cupric acetate gives access to a variety of sulfones in excellent yield.
Beaulieu, Christian,Guay, Daniel,Wang, Zhaoyin,Evans, David A.
p. 3233 - 3236
(2007/10/03)

Ionic liquid-accelerated arylation of sodium arenesulfinates with diaryliodonium salts used for the synthesis of diaryl sulfones
Arylation of sodium arenesulfinates with diaryliodonium salts can be performed with good yields in the room-temperature ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate ([BMim]BF4), which provides an efficient method for the synthesis of diaryl sulfones; the ionic liquid can be recycled and reused.
Wang, Feng-Yan,Chen, Zhen-Chu,Zheng, Qin-Guo
p. 620 - 621
(2007/10/03)

An efficient and convenient method for the synthesis of aromatic sulfones catalysed by ZrO2/S2O82- solid superacid
A manipulatively simple and rapid procedure for the synthesis of diaryl sulfones from arylsulfonyl chlorides with aromatic compounds is described; the reaction is conducted under Friedel-Crafts conditions in the absence of solvent using ZrO2/S2O82- as catalyst in 78-93% yields.
Jin, Tongshou,Yang, Mina,Feng, Guoliang,Li, Tongshuang
p. 721 - 723
(2007/10/03)

Method for acylation or sulphonylation of an aromatic compound
The present invention relates to a process for the acylation or sulphonylation of an aromatic compound. More particularly, the invention relates to a process for the acylation or sulphonylation of an activated or deactivated aromatic compound. The invention is applied to the preparation of aromatic ketones or sulphones. The process for the acylation or sulphonylation of an aromatic compound which consists in reacting at least one aromatic compound with an acylating or sulphonylating agent, in the presence of a Friedel-Crafts catalyst is characterized in that the acylation or sulphonylation reaction is carried out in liquid phase under microwave irradiation.
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(2008/06/13)

Counterion effects in indium-catalysed aromatic electrophilic substitution reactions
Indium(III) triflamide (In(NTf2)3) has been prepared in high yield and has been demonstrated to be an efficient, recoverable catalyst for a range of aromatic electrophilic substitution reactions. When compared to other indium(III) complexes, anomalous reactivities suggest a non-innocent role for the counterion in the studied processes.
Frost, Christopher G,Hartley, Joseph P,Griffin, David
p. 4789 - 4791
(2007/10/03)

A novel method for the synthesis of aryl sulfones
New sulfones were produced from aryl trifluoromethyl sulfones and Grignard reagents in good to high yields. The advantage of this transformation over a previous method by which sulfones were prepared from sulfonyl fluorides and organometallic reagents is discussed.
Steensma, Ruo W.,Galabi, Sharen,Tagat, Jayaram R.,McCombie, Stuart W.
p. 2281 - 2283
(2007/10/03)

An efficient method for aromatic Friedel-Crafts alkylation, acylation, benzoylation, and sulfonylation reactions
Aromatic electrophilic substitution reactions such as alkylation, acylation, benzoylation, and sulfonylation were studied in the presence of a catalytic amount of Cu(OTf)2 and Sn(OTf)2. Cu(OTf)2 was very efficient for alkylation, acylation, and benzoylation reactions. However, in case of sulfonylation reactions, Sn(OTf)2 gave better results.
Singh, Ravi P,Kamble, Rajesh M,Chandra, Kusum L,Saravanan,Singh, Vinod K
p. 241 - 247
(2007/10/03)

Nafion-H catalysed sulfonylation of aromatics with arene/alkenesulfonic acids for the preparation of sulfones
Synthesis of both symmetric and unsymmetric diaryl/aryl alkyl sulfones is easily achieved by Friedel-Crafts type sulfonylation of aromatics with suitable arene- or alkanesulfonic acids in the presence of Nafion-H, a perfluorinated resinsulfonic acid catalyst.
Olah,Mathew,Prakash
p. 1696 - 1697
(2007/10/03)

Indium-catalysed aryl and alkyl sulfonylation of aromatics
Commercially available indium (III) triflate is shown to be an extremely efficient catalyst for the sulfonylation of both activated and deactivated aromatics.
Frost,Hartley,Whittle
p. 830 - 832
(2007/10/03)

Acylation and related reactions under microwaves. 4. Sulfonylation reactions of aromatics
Solvent-free sulfonylation of benzene and its activated or deactivated derivatives were carried out under microwave (MW) irradiation and a catalytic amount of iron(III) chloride, which, under these conditions, is more, active than other metallic salts. With more reactive and/or nonvolatile reagents (anisole, xylenes, mesitylene) expeditious conditions (short reaction time at constant MW power without control of the temperature) were used. With less reactive and/or low-boiling reagents (benzene, toluene, halobenzenes), the rise in temperature and the increase of reaction time were controlled either by sequential MW irradiation or by a temperature order. It was shown that MWs cause preferential interactions with polar species present in the reaction, especially the aryl sulfone and its FeCl3-complexed form. A MW nonthermal effect was not observed when identical temperature gradients were produced by classical heating and MW irradiation, and if reaction temperature was strictly controlled.
Marquie,Laporterie,Dubac,Roques,Desmurs
p. 421 - 425
(2007/10/03)