- 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)
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- Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates
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This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.
- Cheng, Lan,Guo, Jianbo,Li, Yufei,Liang, Xin,Wang, Qingmin,Xia, Qing,Zhang, Pei,Zhang, Weihua
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supporting information
p. 8865 - 8870
(2021/11/30)
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- A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling
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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)
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- Nano copper catalyzed synthesis of symmetrical/unsymmetrical sulfones from aryl/alkyl halides and p-toluenesulfonylmethylisocyanide: TosMIC as a tosyl source
-
A magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of diaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. Sulfones containing molecules have medicinal relevance as they are known to possess various activities such as antifungal, anti-HIV, antitumor, and anticancer. Herein, a magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of biaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. In this newly developed protocol TosMIC acts as sulfonyl source. The catalyst can magnetically be recovered and recycled five times without significant loss in activity.
- Phanindrudu, Mandalaparthi,Jaya, Pogula,Likhar, Pravin R.,Tiwari, Dharmendra Kumar
-
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- TosMIC and its derivatives as versatile sulfonylating agents for the synthesis of p-toluenesulfonylarenes from aryl halides and arylboronic acids
-
An efficient copper(II) catalyzed sulfonyation of aryl halides has been achieved using TosMIC (p-toluenesulfonylmethyl isocyanide) as a sulfonylating agent. This newly developed sulfonylation approach provides an easy access for the synthesis of diaryl sulfones from aryl bromides, iodides and boronic acids with TosMIC under neutral conditions. This method is useful for the sulfonylation of aryl boronic acids under similar conditions. This is the first report on the sulfonylation of aryl bromides, iodides and boronic acids using TosMIC.
- Ravi Kumar,Ramesh,Banik, Swarnayu,Subba Reddy
-
-
- 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.
- -
-
Paragraph 0036-0037
(2019/05/15)
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- Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: Synthesis of (un)symmetrical diaryl/alkyl aryl sulfones
-
We disclose herein the first transition-metal-and external oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from arenediazonium tetrafluoroborates and sodium sulfinates using eosin Y as an organic photoredox catalyst. The utilization of visible light as an inexpensive and ecosustainable energy source, operational simplicity, ambient temperature and clean reaction in aqueous acetonitrile are the salient features of the developed protocol. The desired sulfones were also synthesized via a one-pot, two-step process directly from anilines and sulfinate salts in good to excellent yields.
- Chawla, Ruchi,Yadav, Lal Dhar S.
-
supporting information
p. 4761 - 4766
(2019/05/24)
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- Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
-
An efficient photoredox/nickel catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also includes less reactive aryl chlorides as suitable substrates for this transformation.
- Yue, Huifeng,Zhu, Chen,Rueping, Magnus
-
supporting information
p. 1371 - 1375
(2018/01/27)
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- A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination
-
A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Br?nsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.
- Pandey, Anand Kumar,Kumar, Saurabh,Singh, Rahul,Singh, Krishna Nand
-
supporting information
p. 6704 - 6709
(2018/10/15)
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- 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)
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- Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates
-
A novel nickel-catalyzed cross-coupling of sulfinic acid salts with aryl halides is described. The reaction provides access to various diaryl sulfones in moderate to excellent yields. A broad range of functional groups and heteroaromatic compounds is tolerated under the reaction conditions.
- Liu, Nai-Wei,Liang, Shuai,Margraf, Natalie,Shaaban, Saad,Luciano, Vanessa,Drost, Marcella,Manolikakes, Georg
-
supporting information
p. 1208 - 1210
(2018/03/21)
-
- Design, synthesis, characterization and antimicrobial evaluation of some heterocyclic condensed systems with bridgehead nitrogen from thiazolotriazole class
-
In the present study, a series of new heterocyclic condensed systems with bridgehead nitrogen from the thiazolo[3,2-b][1,2,4]triazoles class was synthesized starting from some 4-(4-X-phenylsulfonyl)phenyl)-4H-1,2,4-triazole-3-thioles 1a-c (X=H, Cl, Br). The intermediates of S-alkylated 1,2,4-triazoles, 2-(5-(4-(4-X-phenylsulfonyl)phenyl)-2H-1,2,4-triazol-3-ylthio)-1-(4-fluorophenyl)ethanones 2a-c, were obtained by treatment of triazoles 1a-c with 2-bromo-4'-fluoroacetophenone. The 2-(4-(4-X-phenylsulfonyl)phenyl)-6-(4-fluorophenyl)thiazolo[3,2-b][1,2,4]triazoles 3a-c were obtained by cyclization of S-alkylated 1,2,4-triazoles 2a-c in sulfuric acid media, at 0°C. For the synthesis of 2-(4-(4-X-phenylsulfonyl)phenyl)-5-(4-fluorobenzylidene)-thiazolo[3,2-b][1,2,4]triazol-6(5H)-ones 4a-c, the triazoles 1a-c were treated with 4-fluorobenzaldehyde, chloroacetic acid and anhydrous sodium acetate, in the presence of acetic acid and acetic anhydride. The structures of the newly synthesized compounds have been confirmed by elemental analysis and spectral methods (IR, 1H-NMR,13C-NMR, MS). The antimicrobial activity of all new compounds has been screened against some bacteria and yeasts.
- Barbuceanu, Stefania-Felicia,Draghici, Constantin,Barbuceanu, Florica,Bancescu, Gabriela,Saramet, Gabriel
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p. 694 - 700
(2015/11/27)
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- Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate
-
Aryl sulfones have been for the first time synthesized by the reaction of sodium p-toluenesulfinate and arenediazonium salts using a CuI catalyzed homogeneous system. The developed protocol is a simple and efficient new route for the synthesis of diaryl sulfones with excellent product yields. The mild reaction conditions tolerate a range of functional groups. The best results were obtained with CuI, N,N′-dimethylethylenediamine, TBAI and K2CO3 in dimethyl sulfoxide at 100°C under an inert atmosphere.
- Gund, Sitaram Haribhau,Shelkar, Radheshyam Suresh,Nagarkar, Jayashree Milind
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p. 62926 - 62930
(2015/08/06)
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- 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
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p. 847 - 852
(2014/04/17)
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- 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)
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- A mild and base-free synthesis of unsymmetrical diaryl sulfones from arylboronic acids and arylsulfonyl hydrazides
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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)
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- A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones
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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
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p. 831 - 836
(2013/06/05)
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- Sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor
-
We have developed Friedel-Crafts (FC) sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor. In this procedure, methyl p-toluenesulfonate was treated and activated with pyridine to produce N-methylpyridinium p-toluenesulfonate as a sulfonylation reagent. Reactivity of this salt for the sulfonylation of mesitylene was investigated in the presence of three different promoters, such as triflic anhydride, dimethylsulfide ditriflate, and triphenylphosphine ditriflate (TPPD). All of the promoters show chemoselectivity and among them, TPPD presents a chemoselectivity in FC sulfonylation. Iranian Chemical Society 2012.
- Khodaei,Nazari
-
p. 507 - 512
(2013/02/22)
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- 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
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experimental part
p. 197 - 203
(2010/11/05)
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- 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)
-
- Copper(II) and uranyl(II) complexes with acylthiosemicarbazide: Synthesis, characterization, antibacterial activity and effects on the growth of promyelocytic leukemia cells HL-60
-
New chelates of N1-[4-(4-X-phenylsulfonyl)benzoyl]-N4-butyl-thiosemicarbazide (X = H, Cl, Br) with Cu2+ and UO22+ have been prepared and characterized by analytical and physico-chemical techniques such as magnetic susceptibility measurements, elemental and thermal analyses, electronic, ESR and IR spectral studies. Room temperature ESR spectra of Cu(II) complexes yield {g} values characteristic of distorted octahedral and pseudo-tetrahedral geometry. Infrared spectra indicate that complexes contain six-coordinate uranium atom with the ligand atoms arranged in an equatorial plane around the linear uranyl group. Effects of these complexes on the growth of human promyelocytic leukemia cells HL-60 and their antibacterial activity (against Staphylococcus epidermidis ATCC 14990, Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 14579, Pseudomonas aeruginosa ATCC 9027 and Escherichia coli ATCC 11775 strains) were studied comparatively with that of free ligands.
- Angelusiu, Madalina Veronica,Almajan, Gabriela Laura,Rosu, Tudor,Negoiu, Maria,Almajan, Eva-Ruxandra,Roy, Jenny
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scheme or table
p. 3323 - 3329
(2009/12/01)
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- 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.
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scheme or table
p. 497 - 503
(2009/05/11)
-
- Identification of diarylsulfone sulfonamides as secreted frizzled related protein-1 (sFRP-1) inhibitors
-
Inhibitor of secreted frizzled related protein-1 (sFRP-1) would be a novel potential osteogenic agent, since loss of sFRP-1 affects osteoblast proliferation, differentiation, and activity, resulting in improved bone mineral density, quality, and strength. We have identified small molecule diarylsulfone sulfonamide derivatives as sFRP-1 inhibitors. Structure-activity relationship generated for various regions of the scaffold was utilized to improve the biochemical profile, resulting in the identification of potent selective analogues, such as 16 with desirable pharmaceutical profile.
- Gopalsamy, Ariamala,Shi, Mengxiao,Stauffer, Barbara,Bahat, Ramesh,Billiard, Julia,Ponce-De-Leon, Helga,Seestaller-Wehr, Laura,Fukayama, Shoichi,Mangine, Annamarie,Moran, Robert,Krishnamurthy, Girija,Bodine, Peter
-
supporting information; experimental part
p. 7670 - 7672
(2009/12/07)
-
- Sulfonylation of arenes with sulfonamides
-
In the presence of triflic anhydride, sulfonylation of arenes with sulfonamides proceeded smoothly in Cl2CHCHCl2 at 80-140 °C, which gave rise to the desired products in good to excellent yields.
- Yao, Bangben,Zhang, Yuhong
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p. 5385 - 5388
(2008/12/21)
-
- Kepner-Tregoe decision analysis as a tool to aid route selection. Part 2. Application to AZD7545, a PDK inhibitor
-
Kepner-Tregoe decision analysis was formally used as an aid to route selection, as outlined in the preceding paper. Over 40 paper routes were assessed for suitability for both immediate and longer term manufacture of AZD7545, a compound in the early stages of development. Eight routes were then investigated in full in the laboratory, and a further four in part, over a period of 3-4 months. From this exercise, the preferred long-term manufacturing route was identified before the first pilot scale manufacture had been completed. This route selection exercise worked well in this case where a large number of potential routes had to be considered using limited resources. It was also an effective means of bringing some long-term manufacturing issues to the fore at an early stage in development.
- Moseley, Jonathan D.,Brown, David,Firkin, Catherine R.,Jenkin, Shelley L.,Patel, Bharti,Snape, Evan W.
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p. 1044 - 1059
(2013/01/03)
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- Copper-Catalyzed Sulfonylation of Arylboronic Acids in Ionic Liquids
-
Cupric acetate in ionic liquids (ILs) catalyzes coupling reaction of arylboronic acids with sulfinic acid salts to afford aryl sulfones in good yields under ambient conditions. This mild and efficient cross-coupling reaction gives access to a wide range of alkylaryl and diaryl sulfones in good yields. The use of ionic liquid allows for easy separation of the product and recycling of copper catalyst.
- Kantam, M. Lakshmi,Neelima,Sreedhar,Chakravarti, Rajashree
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experimental part
p. 1455 - 1458
(2009/04/07)
-
- 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
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p. 3931 - 3934
(2008/09/21)
-
- Cross-coupling of organoboronic acids and sulfinate salts using catalytic copper(II) acetate and 1,10-phenanthroline: synthesis of aryl and alkenylsulfones
-
A mild method for the preparation of aryl and alkenylsulfones from the cross-coupling reaction of organoboronic acids and sodium sulfinate salts is described. Optimized conditions utilize a catalytic amount of copper(II) acetate monohydrate with 1,10-phenanthroline as ligand in the presence of 4 ? molecular sieves. A co-solvent mixture of dichloromethane/DMSO was used, with reactions occurring at 40 °C under an atmosphere of oxygen. Reaction at room temperature also yields sulfone product, but in lower yields. The method tolerates a variety of substituents on the organoboronic acid, including amide, aldehyde, halide and nitro functionalities, as well as ortho-substituents. In general, the reaction is found to be less efficient using arylboronic acids bearing electron-withdrawing substituents, or using aryltrifluoroborate salts.
- Huang, Fang,Batey, Robert A.
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p. 7667 - 7672
(2008/02/08)
-
- 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)
-
- Fe-pillared bentonite-an efficient catalyst for sulfonylation of arenes using aryl and alkyl sulfonyl chlorides
-
Fe-pillared bentonite (Fe-PILC) was shown to be an extremely efficient catalyst for the sulfonylation of activated as well as unactivated carbocyclic aromatic compounds and heterocyclic aromatic compounds. The catalyst was also found to be recyclable.
- Singh, Devendrapratap U.,Singh, Pankajkumar R.,Samant, Shriniwas D.
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p. 9079 - 9082
(2007/10/03)
-
- Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts
-
The palladium-catalyzed reaction of sulfinic acid salts with a wide variety of aryl and vinyl halides or triflates provides unsymmetrical diaryl sulfones and aryl vinyl sulfones in good to excellent yields. The reaction is strongly influenced by the presence of nBu4NCl, and the use of Xantphos, a rigid bidentate ligand with a wide natural bite angle, was found to be crucial for the success of the reaction. With neutral, electron-rich, and electron-poor aryl iodides best results were obtained by using Pd 2(dba)3, Xantphos, Cs2CO3, and nBu4NCl, in toluene at 80 °C. Two general procedures were employed with aryl bromides and triflates: sodium p-toluenesulfinate, Pd2(dba)3, Xantphos, Cs2CO3, 120 °C, in toluene with nBu4NCl (procedure A: neutral, electron-rich, and slightly electron-poor aryl bromides or triflates) and without nBu4NCl (procedure B: electron-poor aryl bromides or triflates). With vinyl triflates best results were obtained at 60 °C omitting nBu4NCl.
- Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Parisi, Luca M.,Bernini, Roberta
-
p. 5608 - 5614
(2007/10/03)
-
- Magnesium perchlorate: An efficient catalyst for selective sulfonylation of arenes under neutral conditions
-
Magnesium perchlorate is found to be an extremely efficient catalyst for the sulfonylation of activated, unactivated and heterocyclic aromatics under almost neutral conditions.
- Bandgar,Kamble,Bavikar
-
p. 287 - 289
(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)
-
- 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)
-
- Sodium periodate catalyzed selective sulfonylation of aromatics
-
Sodium periodate catalyzed sulfonylation of aromatics with p-toluenesulfonyl chloride gives the corresponding sulfones in good yield under neutral conditions.
- Bandgar,Kamble
-
p. 1066 - 1067
(2007/10/03)
-
- Selective sulfonylation of arenes and benzoylation of alcohols using lithium perchlorate as a catalyst under neutral conditions
-
Sulfonylation of aromatics with p-toluenesulfonyl chloride and benzoylation of alcohols with benzoyl chloride using lithium perchlorate as a catalyst is described. The remarkable selectivity under neutral conditions is an attractive feature of this method.
- Bandgar,Kamble,Sadavarte,Uppalla
-
p. 735 - 738
(2007/10/03)
-
- Synthesis of sulfones using sodium perchlorate as a catalyst under neutral conditions
-
Sulfonylation of aromatics with p-toluenesulfonyl chloride in the presence of a catalytic amount of sodium perchlorate gives the corresponding sulfones. Selectivity and neutral condition are the attractive features of this methodology.
- Bandgar,Kamble,Fulse,Deshmukh
-
p. 1105 - 1107
(2007/10/03)
-
- Unsymmetrical Diaryl Sulfones through Palladium-Catalyzed Coupling of Aryl Iodides and Arenesulfinates
-
(Equation Presented) The palladium-catalyzed coupling of aryl iodides and arenesulfinates provides a simple and extremely efficient new route to unsymmetrical diaryl sulfones, usually isolated in high yield. The reaction tolerates a variety of functionalized aryl iodides, including those containing ether, ester, and nitro groups. The best results have been obtained by using Pd2(dba)3, Xantphos, Cs2CO3, and nBu4NCl in toluene at 80 °C.
- Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Parisi, Luca M.
-
p. 4719 - 4721
(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)
-
- Zinc-mediated fast sulfonylation of aromatics
-
Zn dust-mediated Friedel-Crafts sulfonylation of aromatic compounds with p-toluenesulfonyl chloride was carried out to give corresponding sulfones in good yields. Isolation of pure products by simple filtration and evaporation is an important feature of this method.
- Bandgar,Kasture
-
p. 1065 - 1068
(2007/10/03)
-
- An efficient and novel method for the synthesis of aromatic sulfones under solvent - Free conditions
-
A manipulative simple and rapid reaction of arensulfonyl chloride with aromatic hydrocarbons is described. The reaction is conducted under Friedel-Crafts conditions in the absences of solvent using aluminium chloride as catalysts.
- Hajipour,Mallakpour,Imanzadch
-
p. 237 - 239
(2007/10/03)
-
- Organic reactions under solid-state conditions
-
Manipulatively simple and rapid methods are described for the synthesis of: chiral sulfinate esters from sulfonyl chlorides and sufonic acids; aldehydes and ketones from oximes, alcohols, hydrozones; sulfoxides from sulfides; and disulfides from thiols. The chemical yields are good to excellent and diastereoselectivity is high.
- Hajipour,Mallakpour
-
p. 371 - 387
(2007/10/03)
-
- An efficient method for aromatic Friedel-Crafts alkylation, acylation, benzoylation, and sulfonylation reactions
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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
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p. 241 - 247
(2007/10/03)
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- Nafion-H catalysed sulfonylation of aromatics with arene/alkenesulfonic acids for the preparation of sulfones
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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
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p. 1696 - 1697
(2007/10/03)
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- Acylation and related reactions under microwaves. 4. Sulfonylation reactions of aromatics
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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
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p. 421 - 425
(2007/10/03)
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- Friedel - Crafts sulfonylation in 1-Butyl-3-methylimidazolium chloroaluminate ionic liquids
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1-Butyl-3-methylimidazolium chloroaluminate ionic liquids have been employed as an unconventional reaction media and as Lewis acid catalyst for Friedel-Crafts sulfonylation reaction of benzene and substituted benzenes with 4-methyl benzenesulfonyl chloride. The substrates exhibited enhanced reactivity, furnishing almost quantitative yields of diaryl sulfones, under ambient conditions. Studies concerning the effect of Lewis acidity of the ionic liquid on the initial extent of conversion of this reaction has been carried out. 27Al NMR spectroscopy has been exploited as a tool to investigate the mechanistic details of the reaction. 27Al NMR spectral studies show the predominance of [Al2Cl7]- species in [bmim] Cl-AlCl3, N = 0.67, acidic ionic liquid in the presence of 4-methyl benzenesulfonyl chloride, and after the reaction with the aromatic hydrocarbon, [AlCl4]- species predominates. This change in speciation of aluminum can be attributed to the interaction of the Lewis acidic species [Al2Cl7]- of the ionic liquid with the formed HCl during the sulfonylation reaction, which is evidenced by the control experiment. Preliminary investigations on Friedel-Crafts acylation further substantiate the argument.
- Nara,Harjani,Salunkhe
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p. 8616 - 8620
(2007/10/03)
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- Hypervalent iodine in synthesis 67: A convenient method for the synthesis of diaryl sulfones by palladium-catalysed arylation of sodium arenesulfinates with diaryliodonium salts
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In the presence of Ph(PPh3)4, diaryliodonium salts react with sodium arenesulfinates to produce diaryl sulfones in reasonable yields under mild reaction conditions.
- Zhou,Chen
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p. 474 - 475
(2007/10/03)
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- Friedel-Crafts sulfonylation of aromatics catalysed by solid acids: An eco-friendly route for sulfone synthesis
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A mild and efficient catalytic method for Friedel-Crafts sulfonylation of arenes to the corresponding sulfones using a catalytic amount of reusable solid acid and arene- or alkanesulfonyl chlorides, sulfonic anhydrides and sulfonic acids as sulfonylating agents is described. Solid acids enable formation of a sulfone by the reaction of a sulfonic acid and an arene for the first time. In pursuit of the development of the best catalytic system, various metal-exchanged K10 montmorillonites and synthetic zeolites such as zeolite beta, zeolite Y and ZSM-5 have been screened for Friedel-Crafts sulfone synthesis. Fe3+-montmorillonite in the family of clays and zeolite beta in the family of zeolites exhibit higher activity. The activity is correlated to the presence of the right mix of Bronsted and Lewis acidic sites. The regioselective sulfonylation of toluene and naphthalene are studied in which para and beta selectivities are observed respectively. The Royal Society of Chemistry 2000.
- Choudary, Boyapati M.,Chowdari, N. Sreenivasa,Kantam, M. Lakshmi
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p. 2689 - 2693
(2007/10/03)
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- Bismuth(III) halides: Remarkable doping agents for triflic acid in the catalytic sulfonylation of arenes
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The catalytic activity of triflic acid has been dramatically increased by the addition of a catalytic amount of bismuth(III) chloride. Thus, the catalytic sulfonylation of arenes using the new system BiCl3-triflic acid has been successfully carried out while both components of this catalytic system are poorly active or inactive alone, which suggests a synergy between BiCl3 and triflic acid. Other bismuth halide-triflic acid systems proved to be active.
- Repichet,Le Roux,Dubac
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p. 9233 - 9234
(2007/10/03)
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