- Rapid and mild sulfonylation of aromatic compounds with sulfonic acids via mixed anhydrides using Tf2O
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An efficient and direct sulfonylation of aromatic compounds with sulfonic acids is described via mixed anhydrides in short reaction times using Tf2O in nitromethane at room temperature.
- Alizadeh, Abdolhamid,Khodaei, Mohammd Mehdi,Nazari, Ehsan
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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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- Direct sulfonylation of aromatic rings with aryl or alkyl sulfonic acid using supported P2O5/Al2O3
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Direct sulfonylation of aromatic rings with aryl or alkyl sulfonic acid supported P2O5/Al2O3 (w/w 50%) under heterogeneous conditions in short reaction time and high yields. Copyright Taylor & Francis Inc.
- Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Pourmousavi, Seied A.,Mirjalili, Bi Bi F.,Ruoho
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Read Online
- A PROCESS FOR THE SYNTHESIS OF ARYL SULFONES
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The present patent discloses a novel, efficient and transition-metal-free room temperature single step process for synthesis of aryl sulfones and substituted aryl sulfones starting from aryl substrates.
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Page/Page column 9; 12; 14
(2015/06/25)
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- The synthesis of diarylsulfones with simple arenes and K2S2O8 through double C-S bond formation
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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
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supporting information
p. 15037 - 15040
(2014/12/11)
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- Transition-metal-free C-S bond formation: A facile access to aryl sulfones from sodium sulfinates via arynes
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Sulfones have been attractive targets for synthetic organic chemists owing to their immense applications in medicinal, material, and synthetic chemistry. In this context, an efficient transition-metal-free process has been demonstrated, wherein a broad range of alkyl/aryl/heteroaryl sodium sulfinates react with varyingly substituted aryne precursors (o-silyl aryl triflates) under mild reaction conditions to afford structurally diverse sulfones in good to excellent yields.
- Pandya, Virat G.,Mhaske, Santosh B.
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supporting information
p. 3836 - 3839
(2014/08/05)
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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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- 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
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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
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p. 2183 - 2185
(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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- 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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- 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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- An efficient and novel method for the synthesis of aromatic sulfones under solvent - Free conditions
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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
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p. 237 - 239
(2007/10/03)
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- Organic reactions under solid-state conditions
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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
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p. 371 - 387
(2007/10/03)
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- Phthaloperinone dyestuffs
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Phthaloperinone dyestuffs of the general formula (I) STR1 wherein Z denotes SO2 or CO, A represents optionally substituted alkyl or aryl, and the other substituents have the meanings given in the description, are prepared by condensation of corresponding phthalic acids or functional derivatives thereof and optionally substituted 1,8-naphthalene-diamines. The dyestuffs according to the invention have very good fastnesses and are employed in processes for bulk dyeing plastics.
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- Electrochemical Reduction of Some o-Bis(phenylsulphonyl)benzene Derivatives. Effect of the Substrate Structure and of the Addition of Bases on the Product Distribution.
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A study of the electrochemical behaviour of the o-bis(phenylsulphonyl)benzene derivatives (1a-e) in dimethyl sulphoxide containing 0.1M-tetrabutylammonium tetrafluoroborate has been undertaken.The results from cyclic voltammetry, controlled-potential electrolysis, and coulometry strongly argue in support of a mechanism involving initial formation of the radical anion (1)-. which fragments into the ? radical (2) and PhSO2-.Competing pathways for (2) are (a) intramolecular homolytic arylation eventually leading to dibenzothiophene (4) together with dihydrodibenzothiophene (5) derivatives and (b) hydrogen-atom transfer leading to monosulphones (6).The fact that compounds (1a,b) undergo mainly cyclization, whereas the hydrogen-atom transfer predominates in the case of compounds (1c,d), indicates that the structure of the starting substrate is a major governing factor for the above competition.An explanation, based on a concomitance of steric effects of the methyl groups ortho to the phenylsulphonyl substituents, is given.Experiments carried out in the presence of different bases show that the intramolecular arylation leading to the cyclized product can occur also through an unprecedented chain mechanism whose efficiency, which increases as the strength and the concentration of the base is increased, is found in turn to be dependent on the substrate structure.Finally, when arenethiolates are used as bases, a third pathways (the nucleophile-radical coupling step of the SRN1 process) is found to compete for the intermediate ? radical (2) eventually leading to sulphides resulting from the overall substitution of an arylthio for a moiety in (1).When the intramolecular cyclization does not compete efficiently almost quantitative yields of sulphides are obtained via an SRN1 route.
- Novi, Marino,Garbarino, Giacomo,Petrillo, Giovanni,Dell'Erba, Carlo
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p. 623 - 632
(2007/10/02)
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