cas 98-09-9, Benzenesulfonyl chloride | Articles data

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Wittmann et al.
p. 734
(1969)
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On the reactivity of (7-oxabicyclo[2.2.1]hept-5-en-2-ylidene)amines. Different reaction paths leading to the same final products
The reaction of amines, N-substituted by a 7-oxabicycIo[2.2.1]hept-5-en-2-ylidene moiety, either with PhSCl or mCPBA (meta-chloroperbenzoic acid) unexpectedly afforded the same type of furan derivatives by two different reaction paths. The results confirm the intervention of a homoconjugative, electron-releasing effect of the oxabicycloalkenylideneamine moieties, as predicted theoretically.
Arjona, Odon,Csaky, Aurelio G.,Murcia, M. Carmen,Plumet, Joaquin
p. 3667 - 3672
(2001)
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Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst
Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.
Antonietti, Markus,Guldi, Dirk M.,Markushyna, Yevheniia,Savateev, Aleksandr,Schü?lbauer, Christoph M.,Ullrich, Tobias
supporting information
p. 20543 - 20550
(2021/08/12)

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
supporting information
p. 8338 - 8342
(2021/10/25)

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
(2021/09/20)

High purity synthetic method of benzene sulfonyl chloride (by machine translation)
The invention discloses a high-purity benzene sulfonyl chloride synthesis method, comprises the following steps: (1) in order to acid as the raw material, the reaction to prepare the benzenesulphonate; (2) the step (1) synthesized in the benzenesulphonate through recrystallization purification method, the impurity is removed to obtain the benzenesulphonate; (3) the step (2) in the purification of the benzenesulphonate in solvents and chlorinated reagent reaction to prepare the benzene sulfonyl chloride. Through the above-mentioned way, the present invention can prepare for obtaining high-purity benzene sulfonyl chloride product, its purity can be up to 99.9%, medical and electronic chemicals can meet the requirements of production. (by machine translation)
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Paragraph 0016-0025

(2019/03/31)

Proline-Based Allosteric Inhibitors of Zika and Dengue Virus NS2B/NS3 Proteases
The NS2B/NS3 serine proteases of the Zika and Dengue flaviviruses are attractive targets for the development of antiviral drugs. We report the synthesis and evaluation of a new, proline-based compound class that displays allosteric inhibition of both proteases. The structural features relevant for protease binding and inhibition were determined to establish them as new lead compounds for flaviviral inhibitors. Based on our structure-activity relationship studies, the molecules were further optimized, leading to inhibitors with submicromolar IC50 values and improved lipophilic ligand efficiency. The allosteric binding site in the proteases was probed using mutagenesis and covalent modification of the obtained cysteine mutants with maleimides, followed by computational elucidation of the possible binding modes. In infected cells, antiviral activity against Dengue virus serotype 2 using prodrugs of the inhibitors was observed. In summary, a novel inhibitor scaffold targeting an allosteric site shared between flaviviral NS2B/NS3 proteases is presented whose efficacy is demonstrated in vitro and in cellulo.
Millies, Benedikt,Von Hammerstein, Franziska,Gellert, Andrea,Hammerschmidt, Stefan,Barthels, Fabian,G?ppel, Ulrike,Immerheiser, Melissa,Elgner, Fabian,Jung, Nathalie,Basic, Michael,Kersten, Christian,Kiefer, Werner,Bodem, Jochen,Hildt, Eberhard,Windbergs, Maike,Hellmich, Ute A.,Schirmeister, Tanja
p. 11359 - 11382
(2019/12/24)

Preparation method for symmetric diaryl disulfide
The invention discloses a preparation method for symmetric diaryl disulfide. The preparation method comprises the following steps: using aromatic hydrocarbon as shown in a general formula (I) as a rawmaterial and reacting with chlorosulfonic acid to generate aryl chlorosulfonic acid, and reacting with sulfoxide chloride to synthesize aryl sulfonyl chloride as shown in a general formula (II); andpreparing the symmetric diaryl disulfide as shown in a general formula (III) under the action of a reducing agent through a reduction reaction by the aryl sulfonyl chloride as shown in the general formula (II). The disclosed preparation method for the symmetric diaryl disulfide has many advantages of low toxicity of the reaction raw material, short reaction time, cheap reagents and easy acquisition, convenient separation and purification and the like, and has very high application value and industrial production value.
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Paragraph 0038; 0039; 0040; 0041

(2019/04/17)

High yielding protocol for direct conversion of thiols to sulfonyl chlorides and sulfonamides
In this paper, a new method for oxidative chlorination of thiols to sulfonyl chlorides and sulfonamides using H2O2 in the presence of TMSCl is reported. The excellent yields, short reaction times, excellent efficiencies, low costs, and easy separation of products are the most important advantages of this method.
Sohrabnezhad, Samira,Bahrami, Kiumars,Hakimpoor, Farahman
p. 256 - 264
(2019/02/06)

Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.
Jereb, Marjan,Hribernik, Luka
supporting information
p. 2286 - 2295
(2017/07/24)

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
supporting information
p. 2244 - 2247
(2017/05/16)

Aromatic Chlorosulfonylation by Photoredox Catalysis
Visible-light photoredox catalysis enables the efficient synthesis of arenesulfonyl chlorides from anilines. The new protocol involves the convenient in situ preparation of arenediazonium salts (from anilines) and the reactive gases SO2and HCl (from aqueous SOCl2). The photocatalytic chlorosulfonylation operates at mild conditions (room temperature, acetonitrile/water) with low catalyst loading. Various functional groups are tolerated (e.g., halides, azides, nitro groups, CF3, SF5, esters, heteroarenes). Theoretical and experimental studies support a photoredox-catalysis mechanism.
Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel
p. 151 - 155
(2017/01/17)

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides
A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.
Yang, Zhanhui,Xu, Wei,Wu, Qiuyue,Xu, Jiaxi
p. 3051 - 3057
(2016/04/26)

Preparation method benzene sulfonyl chloride and diphenylsulfone
The invention discloses a preparation method of benzene sulfonyl chloride and diphenylsulfone. The method comprises the following steps: 1) sulfonation: adding chlorosulfonic acid into a sulfonation reaction kettle, dropwisely adding benzene, controlling the temperature at 60 DEG C or below, and after finishing the dropwise addition, keeping the temperature for 1 hour, thereby obtaining a sulfonation product; 2) hydrolysis and stratification: adding the sulfonation product and excessive chlorosulfonic acid into a hydrolysis reaction kettle, dropwisely adding water, controlling the temperature at 60 DEG C or below, stirring for 30 minutes after finishing the dropwise addition, standing for stratification, and separating the sulfuric acid layer, wherein the organic layer enters a neutralization reaction kettle; 3) neutralization and stratification: introducing the organic layer into the neutralization reaction kettle, adding liquid caustic soda, regulating the pH value to a neutral state, standing for stratification, and separating the water layer; and 4) rectification: introducing the organic layer into a rectification reaction kettle, heating to perform rectification under vacuum, collecting the product benzene sulfonyl chloride at 150 DEG C under the pressure of -0.098 MPa, and obtaining the rectification residue diphenylsulfone. The method greatly improves the working environment, and has higher economic benefits.
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Paragraph 0011; 0012

(2016/12/26)

New process for the production of arensulfonyl chloride from arensulfonic acid
The present invention refers to degradation of a fine chemicals functionalised in a synthetic process of intermediates to conversion of an important role new manufacturing method relates to a novel process of arylsulfonyl, arylsulfonyl chloride hour draw from previous techniques are nick biting opinion gun method for producing [...] the users determine a structure of basic presents at 70 degree or more time and an elongated reactant hot reaction of undesirable and uniform reaction conditions to improve power efficiency nick biting opinion gun a dilute bis (trichloromethyl) polycarbonate and a catalytic amount of potassium and phosphoric acid incorporated tetrahedral amorphous [...] triethylamine and tree hereinafter also 25 reacting under a condition of gently arylsulfonyl chloride characterized by high yield in the dye by providing new method, pesticide, medicine, as well as related industrial electronic materials of the field will hole is compressed by the reciprocal movement.
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Paragraph 0032; 0033

(2016/12/26)

METHOD FOR PRODUCING SULFONYL CHLORIDE COMPOUNDS
PROBLEM TO BE SOLVED: To provide a production method which enables safe and simple production of sulfonyl chloride compounds in high yields, which are useful as intermediates for medicines, agrochemicals, functional materials, and the like. SOLUTION: Provided is a method for producing sulfonyl chloride compounds comprising oxidation of thiols or disulfides in the presence of an oxidizing agent to produce sulfonyl chloride compounds. As the oxidizing agent is used sodium hypochlorite, and the reaction is performed with the pH of the reaction system adjusted to a neutral or acidic value of pH 7 or less. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0028; 0030

(2018/11/22)

An efficient method for the preparation of sulfonyl chlorides: Reaction of disulfides or thiols with sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals
The reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid efficiently provided the corresponding sulfonyl chlorides in high yields.
Okada, Tomohide,Matsumuro, Hiroaki,Iwai, Toshiaki,Kitagawa, Saori,Yamazaki, Kento,Akiyama, Tomomi,Asawa, Tomotake,Sugiyama, Yukihiro,Kimura, Yoshikazu,Kirihara, Masayuki
p. 185 - 187
(2015/02/19)

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
p. 3125 - 3131
(2014/06/10)

Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.
Li, Wanfang,Beller, Matthias,Wu, Xiao-Feng
p. 9513 - 9516
(2014/08/18)

An improved method for the fluorination of arylsulfur chlorotetrafluorides to arylsulfur pentafluorides
A new method for the fluorination of arylsulfur chlorotetrafluorides to arylsulfur pentafluorides is described. The reaction is promoted by hydrogen fluoride generated from potassium hydrogen fluoride and trifluoroacetic acid which also serves as a solvent. The reaction is performed under mild conditions and uses substochiometric amounts of potassium hydrogen fluorides in certain cases. Recovery and reuse of trifluoroacetic acid was successfully demonstrated which makes this method safe, simple to use, and atom- and cost-effective.
Lummer, Katrin,Ponomarenko, Maxim V.,R?schenthaler, Gerd-Volker,Bremer, Matthias,Beier, Petr
p. 79 - 83
(2014/01/06)

Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
supporting information
p. 2165 - 2169
(2013/10/22)

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA
A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.
Hemmati, Saba,Mojtahedi, Mohammad Majid,Abaee, Mohammad Saeed,Vafajoo, Zahra,Saremi, Shokufe Ghahri,Noroozi, Mohammad,Sedrpoushan, Alireza,Ataee, Meral
p. 347 - 357
(2013/09/23)

One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
p. 2147 - 2151
(2013/12/04)

Electrophilic fluorination of N,N-dimethylaniline, N,N-dimethylnaphthalen- 1-amine and 1,8-bis(dimethylamino)naphthalene with N-F reagents
Reaction of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)- naphthalene (proton sponge) with 1-chloromethyl-4- fluorodiazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) and N-fluorobenzenesulfonimide (NFSI) h
Sorokin, Vladimir I.,Pozharskii, Alexander F.,Ozeryanskii, Valery A.
p. 67 - 72
(2013/11/06)

Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
p. 10638 - 10641
(2013/08/23)

Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) as efficient reagents for the direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
Trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS) were found to be mild and efficient reagents for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good-to-excellent yields through the oxidative chlorination. The overall process is simple and practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides. Copyright
Veisi, Hojat,Sedrpoushan, Alireza,Hemmati, Saba,Kordestani, Davood
experimental part
p. 769 - 775
(2012/06/30)

Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
experimental part
p. 316 - 322
(2012/03/26)

Convenient one-pot synthesis of sulfonamides from thiols and disulfides using 1,3-dichloro-5,5-dimethylhydantoin (DCH)
A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.
Veisi, Hojat
experimental part
p. 383 - 386
(2012/04/23)

Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4
A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.
Bahrami, Kiumars,Khodaei, Mohammad M.,Khaledian, Donya
experimental part
p. 354 - 358
(2012/01/19)

Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system
Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.
Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
supporting information; experimental part
p. 5095 - 5101
(2012/07/28)

ORGANIC COMPOUND AND PHOTOVOLTAIC DEVICE COMPRISING THE SAME
The present invention provides a organic compound of the general structural formula 1 and photovoltaic device and photovoltaic layer comprising thereof Said organic compound forms rod-like supramolecules and absorbs electromagnetic radiation in at least one predetermined spectral subrange within a wavelength range from 400 to 3000 nm with excitation of electron-hole pairs. The polycyclic core Cor1, the bridging group B, and the polycyclic core Cor2 form a molecular system selected from the list comprising donor-bridge-acceptor-bridge-donor and acceptor-bridge-donor-bridge-acceptor in which a dissociation of excited electron-hole pairs is carried out. A solution of the organic compound or its salt forms a solid photovoltaic layer on a substrate.
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(2012/09/22)

TAPC-promoted synthesis of sulfonyl chlorides from sulfonic acids
A novel and efficient method is described for the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, shorter reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications. Georg Thieme Verlag Stuttgart · New York.
Bahrami, Kiumars
experimental part
p. 2671 - 2674
(2011/12/04)

Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as efficient reagents to direct oxidative conversion of thiols and disulfide to sulfonyl chlorides
Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3- disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through the oxidative chlorination. The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
Veisi, Hojat,Ghorbani-Vaghei, Ramin,Mahmoodi, Jafar
experimental part
p. 3692 - 3695
(2012/01/11)

New synthesis of alkane- and arylsulfonyl chlorides by oxidation of thiols and disulfi des with chlorine dioxide
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Lezina,Rubtsova,Kuchin
experimental part
p. 1249 - 1251
(2011/12/01)

Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
experimental part
p. 2315 - 2320
(2011/10/13)

DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation
The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.
Woolven, Holly,Gonzalez-Rodriguez, Carlos,Marco, Isabel,Thompson, Amber L.,Willis, Michael C.
supporting information; experimental part
p. 4876 - 4878
(2011/12/05)

A general and mild two-step procedure for the synthesis of aryl and heteroaryl sulfonamides from the corresponding iodides
A mild two-step preparation of aryl and heteroaryl sulfonyl chlorides and sulfonamides from their corresponding iodides is developed. Acid labile functionalities are shown to be stable under both the copper-catalysed coupling and the subsequent oxidative chlorination.
Ho, Danny K.H.,Chan, Lily,Hooper, Alice,Brennan, Paul E.
scheme or table
p. 820 - 823
(2011/03/18)

A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides
2,4-Dichloro-5,5-dimethylhydantoin (DCDMH) was found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through oxidative chlorination. The method is suitable for many types of sulfur substrates (thiols, disulfides, and benzylic sulfides). The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.
Pu, Yu-Ming,Christesen, Alan,Ku, Yi-Yin
supporting information; experimental part
p. 418 - 421
(2010/03/04)

A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4
Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement
Kim, Joong-Gon,Jang, Doo Ok
experimental part
p. 3049 - 3052
(2011/02/25)

Reactive sulfur species: Kinetics and mechanism of the oxidation of aryl sulfinates with hypochlorous acid
The mechanism of oxidation of ArSO2- (PhSO2 - and 5-sulfinato-2-nitrobenzoic acid = TNBO2 1-/2-) with HOCl/OCl- has been investigated using the kinetic method. In contrast to previous reports for PhSO2- (for which it was suggested that OCl- and not HOCl was the reactant), the reaction proceeds through a conventional pathway: nucleophilic attack by ArSO2- on HOCl with concomitant Cl- transfer to give a sulfonyl chloride intermediate (ArSO2Cl), which we have identified spectrophotometrically. Remarkably, the rate constant for the reaction of HOCl with ArSO2- is on the order of 10 9 M-1 s-1, larger than the rate constants for corresponding thiolates, and is nearly diffusion-controlled. In contrast, the rate constant for the reaction of OCl- with ArSO2 - is approximately 7 orders of magnitude smaller.
Ueki, Hisanori,Chapman, Garry,Ashby, Michael T.
experimental part
p. 1670 - 1676
(2010/08/05)

Development of an extremely efficient oxidative chlorination reaction: The value of routine data collection
This contribution describes the development of an extremely efficient process for the oxidative chlorination of a benzyl, alkyl thioether to yield an alkylsulfonyl chloride. This process was subsequently run on >100 kg scale. The product alkylsulfonyl chloride was required as an intermediate, being used by several drug projects, to prepare sulfonamides. Routine data collection and reaction profiling has led to understanding, which has allowed an alternative reaction pathway to be exploited for the development of a two-step, oxidation-chlorination process. The scope of this new two-step process was briefly examined. The results of this study have allowed us to propose an empirical method for predicting the course of these oxidative chlorination reactions. During these studies we have developed a simple laboratory rig, constructed from inexpensive, readily available equipment, which allows the controlled accurate delivery of known volumes (100s of milliliters) of chlorine gas at a given rate. In our laboratories, this has made the use of gaseous chlorine a considerably less onerous task. This work is testimony to the fruit which may be borne from attempts to gain process understanding, even of an already high-yielding reaction.
Barnwell, Neil,Cornwall, Philip,Horner, Daniel,Knott, Jason,Liddon, John
supporting information; experimental part
p. 278 - 288
(2010/04/29)

(Arylsulfonyl)acetones and -acetonitriles: New activated methylenic building blocks for synthesis of 1,2,3-triazoles
β-Keto sulfones and b-nitrile sulfones were used as building blocks for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. Georg Thieme Verlag Stuttgart.
Pokhodylo, Nazariy T.,Matiychuk, Vasyl S.,Obushak, Mykola D.
scheme or table
p. 2321 - 2323
(2010/02/16)

A novel, practical synthesis of sulfonyl chlorides from thiol and disulfide derivatives
Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiol and disulfide derivatives into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method.
Bahrami, Kiumars,Khodaei, Mohammad Mehdi,Soheilizad, Mehdi
experimental part
p. 2773 - 2776
(2010/02/28)

Direct conversion of thiols to sulfonyl chlorides and sulfonamides
(Chemical Equation Presented) H2O2 in combination with SOCl2 proved to be a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields and in very short reaction times.
Bahrami, Kiumars,Khodaei, Mohammad M.,Soheilizad, Mehdi
supporting information; experimental part
p. 9287 - 9291
(2010/03/04)

An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids
(Chemical Equation Presented) An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.
De Luca, Lidia,Giacomelli, Giampaolo
p. 3967 - 3969
(2008/09/19)

Chlorotrimethylsilane-nitrate salts as oxidants: Direct oxidative conversion of thiols and disulfides to sulfonyl chlorides
(Chemical Equation Presented) A mixture of nitrate salt and chlorotrimethylsilane is found to be a mild and efficient reagent for the direct oxidative conversion of thiols (1) and disulfides (2) to the corresponding sulfonyl chlorides (3) in excellent yields through oxidative chlorination. Sulfides and sulfoxides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases these reactions are highly selective, simple, and clean, affording products in high yield and purity.
Prakash, G. K. Surya,Mathew, Thomas,Panja, Chiradeep,Olah, George A.
p. 5847 - 5850
(2008/02/09)

Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation
Oxidation of several thiol derivatives by a combination of N-chlorosuccinimide and dilute hydrochloric acid proceeded smoothly, affording the corresponding sulfonyl chlorides in good yield. Georg Thieme Verlag Stuttgart.
Nishiguchi, Atsuko,Maeda, Kazuhiro,Miki, Shokyo
p. 4131 - 4134
(2008/03/13)

A practical and efficient method for the preparation of sulfonamides utilizing Cl3CCN/PPh3
Cl3CCN in combination with PPh3 proved to be a highly reactive reagent for the conversion of sulfonic acids to the corresponding sulfonyl chlorides in refluxing CH2Cl2. Upon reaction with amines, the corresponding sulfonamides were obtained in good to excellent yields.
Chantarasriwong, Oraphin,Jang, Doo Ok,Chavasiri, Warinthorn
p. 7489 - 7492
(2007/10/03)

Reaction of arendiazonium salts and SO2with α-nitroolefins
In reaction of β-nitrostyrene and 2-(2-nitrovinyl)furan with arenediazonium chlorides and SO2 in the presence of copper(II) chloride products were obtained resulting from addition of arylsulfonyl group and a hydrogen atom across the C=C bond: 2-nitro-1-phenylethylsulfonylarenes and 2-(1-arylsulfonyl-2-nitroethyl)furans respectively. An anion-radical mechanism of the reaction was suggested.
Bilaya,Obushak,Buchinskii,Ganushchak
p. 191 - 194
(2007/10/03)

A new, mild preparation of sulfonyl chlorides
A new method was developed for the preparation of sulfonyl chlorides from sulfonic acids under neutral conditions using 2,4,6-trichloro-1,3,5-triazine as chlorinating agent.
Blotny, Grzegorz
p. 1499 - 1501
(2007/10/03)

Process for functionalising a phenolic compound carrying an electron-donating group
The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.
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(2008/06/13)

Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides
A series of arene and heteroarene sulfonamides were prepared in one vessel from aryl and heteroaryl bromides via conversion into the corresponding Grignard reagents using either magnesium or isopropylmagnesium chloride and subsequent reaction with sulfur dioxide, sulfuryl chloride, and an amine.
Pandya, Rina,Murashima, Takashi,Tedeschi, Livio,Barrett, Anthony G. M.
p. 8274 - 8276
(2007/10/03)