- Novel Solvent-Free Reactions with Iodine: Solid-Solid and Solid-Vapor Reactions of 1-Aryl-4-(methylthio)-2-(p-tolylsulfonyl)-1,3-butadienes
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Under solvent-free solid-solid and solid-vapor conditions, 1-aryl-4-(methylthio)-2-(p-tolylsulfonyl)-1,3-butadienes (1) react with iodine to form (p-tolylsulfonyl)naphthalene derivatives (2) in high yield. These conditions make the reaction tolerant to the kind of the aryl so that various derivatives of 2 were produced in high yield. The products (2) can be obtained in a nearly pure form by removing co-existing hydrogen iodide and dimethyl disulfide by evaporation. Thus, this process is environmentally benign, because no solvent and water need to get the pure product.
- Matsumoto, Shoji,Kumazawa, Kazuhisa,Ogura, Katsuyuki
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- Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides
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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
- Zhen, Jingsong,Du, Xian,Xu, Xiaohong,Li, Yihui,Yuan, Han,Xu, Dejing,Xue, Can,Luo, Yong
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p. 1986 - 1991
(2022/02/07)
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- Catalyst-free arylation of sulfonamidesviavisible light-mediated deamination
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A novel arylation of sulfonamides with boronic acids to afford numerous diaryl sulfonesviaa visible light-mediated N-S bond cleavage other than the typical transition-metal-catalyzed C(O)-N bond activation is described. This methodology, which represents the first catalyst-free protocol for the sulfonylation of boronic acids, is characterized by its simple reaction conditions, good functional group tolerance and high efficiency. Several successful examples for the late-stage functionalization of diverse sulfonamides indicate the high potential utility of this method in pharmaceutical science and organic synthesis.
- Ding, Hao,Ding, Qiuping,Du, Xian,Li, Yi-Hui,Liu, Bing-Zhe,Lu, Shi-Man,Luo, Yong,Qi, Wan-Ying,Xu, Xiao-Hong,Xue, Can,Yuan, Han,Zhen, Jing-Song
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p. 9556 - 9560
(2021/07/25)
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- Nano copper catalyzed synthesis of symmetrical/unsymmetrical sulfones from aryl/alkyl halides and p-toluenesulfonylmethylisocyanide: TosMIC as a tosyl source
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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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- Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: Synthesis of (un)symmetrical diaryl/alkyl aryl sulfones
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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.
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supporting information
p. 4761 - 4766
(2019/05/24)
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- Regiospecific Cleavage of S-N Bonds in Sulfonyl Azides: Sulfonyl Donors
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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
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p. 3919 - 3926
(2019/03/29)
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- A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination
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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
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supporting information
p. 6704 - 6709
(2018/10/15)
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- Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates
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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
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supporting information
p. 1208 - 1210
(2018/03/21)
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- Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
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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
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supporting information
p. 1371 - 1375
(2018/01/27)
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- An efficient Cu-catalyzed microwave-assisted synthesis of diaryl sulfones
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An efficient and microwave-assisted simple protocol for the synthesis of symmetrical/asymmetrical diaryl sulfones through the Cu(II)-catalyzed reaction of sodium salt of sulfinic acid with aryl boronic acid has been described. Various diaryl sulfones have been synthesized in very short reaction times with moderate to very good yields. Additionally, the method is also useful for the synthesis of aryl vinyl sulfones.
- Nandi, Ganesh C.
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supporting information
p. 319 - 323
(2017/02/10)
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- Synthesis of diaryl sulfones at room temperature: Cu-catalyzed cross-coupling of arylsulfonyl chlorides with arylboronic acids
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An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu-catalyzed cross-couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air. This method is characterized by the use of inexpensive and readily available catalyst and substrates, mild reaction conditions, wide functionality tolerance, short reaction times for most substrates, and moderate to good yields. Stitch it up with copper: An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu-catalyzed cross- couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air.
- Hu, Feng,Lei, Xiangyang
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p. 1539 - 1542
(2015/05/27)
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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
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supporting information
p. 1163 - 1167
(2014/05/20)
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- Sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor
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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
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p. 507 - 512
(2013/02/22)
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- Palladium-catalyzed aromatic sulfonylation: A new catalytic domino process exploiting in situ generated sulfinate anions
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Allylic sulfones are excellent precursors of aryl sulfones via a new Pd-catalyzed domino sequence involving in situ generation of sulfinate anions and subsequent cross-coupling with aryl -iodides or bromides. Georg Thieme Verlag Stuttgart · New York.
- Le Duc, Ga?tan,Bernoud, Elise,Prestat, Guillaume,Cacchi, Sandro,Fabrizi, Giancarlo,Iazzetti, Antonia,Madec, David,Poli, Giovanni
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supporting information; experimental part
p. 2943 - 2946
(2012/01/05)
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- Sulfonylation of aromatic compounds with sulfonic acids using silica gel-supported AlCl3 as a heterogeneous Lewis acid catalyst
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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
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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
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experimental part
p. 1887 - 1890
(2010/11/18)
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- Highly selective catalytic Friedel-Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid
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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)
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- Sulfonylation of arenes with sulfonamides
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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)
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- Synthesis and biological evaluation of novel sulfonyl-naphthalene-1,4-diols as FabH inhibitors
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A series of analogs of 2-tosylnaphthalene-1,4-diol were prepared and were found to be potent 10-20 nM reversible inhibitors of the Escherichia coli FabH enzyme. The inhibitors were also effective but to a lesser degree (30 nM-5 μM), against the Mycobacter
- Alhamadsheh, Mamoun M.,Waters, Norman C.,Sachdeva, Sarbjot,Lee, Patricia,Reynolds, Kevin A.
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supporting information; experimental part
p. 6402 - 6405
(2009/09/30)
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- Cross-coupling of organoboronic acids and sulfinate salts using catalytic copper(II) acetate and 1,10-phenanthroline: synthesis of aryl and alkenylsulfones
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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)
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- Fe-pillared bentonite-an efficient catalyst for sulfonylation of arenes using aryl and alkyl sulfonyl chlorides
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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)
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- Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts
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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
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p. 5608 - 5614
(2007/10/03)
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- An efficient palladium-catalyzed synthesis of unsymmetrical diaryl sulfones from aryl bromides/triflates and arenesulfinates
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The palladium-catalyzed coupling of arenesulfinate salts and aryl bromides or triflates provides a simple and extremely efficient route to unsymmetrical diaryl sulfones. The reaction was found to be strongly influenced by the presence of n-Bu4NCl. The ammonium salt tends to favor the formation of sulfones with neutral, electron-rich and slightly electron-poor aryl bromides or triflates and to hamper the reaction with electron-poor aryl bromides or triflates.
- Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Parisi, Luca M.
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p. 361 - 364
(2007/10/03)
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- An efficient and convenient method for the synthesis of aromatic sulfones catalysed by ZrO2/S2O82- solid superacid
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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
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p. 721 - 723
(2007/10/03)
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- Magnesium perchlorate: An efficient catalyst for selective sulfonylation of arenes under neutral conditions
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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
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p. 287 - 289
(2007/10/03)
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- Selective sulfonylation of arenes and benzoylation of alcohols using lithium perchlorate as a catalyst under neutral conditions
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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
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p. 735 - 738
(2007/10/03)
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- Sodium periodate catalyzed selective sulfonylation of aromatics
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Sodium periodate catalyzed sulfonylation of aromatics with p-toluenesulfonyl chloride gives the corresponding sulfones in good yield under neutral conditions.
- Bandgar,Kamble
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p. 1066 - 1067
(2007/10/03)
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- Synthesis of sulfones using sodium perchlorate as a catalyst under neutral conditions
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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
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p. 1105 - 1107
(2007/10/03)
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- 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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- New construction of p-tolylsulfonyl-substituted naphthalenes by thermal and photochemical cyclization of 1-aryl-4-(methylthio)-2-(p-tolysulfonyl)-1,3-butadienes
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Transformation of 4-(methylthio)-1-phenyl-2-(p-tolysulfonyl)-1,3-butadiene 1a was found to give 2-(p-tolysulfonyl)naphthalene 3a either by the action of I2 in refluxing acetonitrile or by irradiation with a high-pressure Hg lamp. An electron-wi
- Matsumoto, Shoji,Takahashi, Shinjiro,Ogura, Katsuyuki
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p. 385 - 391
(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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- A new route towards the synthesis of substituted naphthalenes via Friedel-Crafts acylation
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A novel approach towards the synthesis of substituted naphthalene derivatives is achieved by a treatment of the 4-aryl-4-hydroxy-3-p- toluenesulfonylbutanal ethylene acetals (6a-e) with a catalytic amount of p- toluene sulfonic acid. (C) 2000 Elsevier Science Ltd.
- Kao, Chai-Lin,Yen, Shu Y.,Chern, Ji-Wang
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p. 2207 - 2210
(2007/10/03)
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- Fe(III) exchanged montmorillonite: A mild and ecofriendly catalyst for sulfonylation of aromatics
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Fe(III) exchanged montmorillonite clay catalyses Friedel-Crafts sulfonylation of arenes with arylsulfonyl chlorides to obtain the corresponding sulfones in excellent yields.
- Choudary,Chowdari, N. Sreenivasa,Kantam, M. Lakshmi,Kannan
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p. 2859 - 2862
(2007/10/03)
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- A KINETIC STUDY OF THE FRIEDEL-CRAFTS REACTION OF NAPHTHALENE WITH PARA- SUBSTITUTED BENZENESULPHONYL CHLORIDES: THE EFFECT OF THE SUBSTITUENT
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The kinetics of the Friedel-Crafts reaction of naphthalene with para-substituted benzenesulphonyl chlorides have been investigated.The rate constants for equations (i) (formation of the sulphonyl cation) and (ii) (sulphone formation) were determined separately.The effect of the para-substituents on k1 was XC6H4SO2Cl + AlCl3 XC6H4SO2+*AlCl4- , XC6H4SO24*AlCl4- + C10H8 XC6H4SO2C10H7*AlCl3 + HCl well expressed by Yukawa-Tsuno equation, log(k1X/K1H)= ρ1(Δ?R(+))> where ρ1= -2.7 and γ1= 0.4.On the other hand, the effect of the para-substituents on k3(=k1k2/k-1) was expressed by the Brown-Okamoto equation, log(k3X/k3H)= ρ3?+ where ρ3= -2.8.Thus, the electron-donating para-substituents gave the greater reaction rates.We concluded that the sulphonyl cation gives large negative ρ values as a result of its high reactivity, and that its low selectivity for α-attack is due to a steric effect.These kinetic results have been rationalised in terms of bifunctional acid-base catalysis in phenylsulphonnylation.
- Yoshii, Yoshihiro,Ito, Akiyoshi,Hirashima, Tsuneaki,Shinkai, Seiji,Manabe, Osamu
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p. 777 - 782
(2007/10/02)
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