cas 6339-26-0, 4-[(4-methylphenyl)sulphonyl]morpholine

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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)

AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST
The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.
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Paragraph 0033-0037; 0039-0054; 0066-0069; 0145-0146

(2021/04/06)

Primary Sulfonamide Functionalization via Sulfonyl Pyrroles: Seeing the N?Ts Bond in a Different Light
Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.
Ozaki, Tomoya,Yorimitsu, Hideki,Perry, Gregory J. P.
p. 15387 - 15391
(2021/10/04)

S(vi) in three-component sulfonamide synthesis: Use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki-Miyaura coupling
Sulfuric chloride is used as the source of the -SO2- group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki-Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. This journal is
Wang, Xuefeng,Yang, Min,Ye, Shengqing,Kuang, Yunyan,Wu, Jie
p. 6437 - 6441
(2021/05/19)

Hydrogen-Bonding Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers over Ionic Liquid under Metal-Free Conditions
O-heterocycles have wide applications, and their efficient and green synthesis is very interesting. Herein, we report hydrogen-bonding catalyzed ring-closing metathesis of aliphatic ethers to O-heterocycles over ionic liquid (IL) catalyst under metal- and solvent-free conditions. The IL 1-butylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3H-BMIm][OTf]) is discovered to show outstanding performance, better than the reported catalysts. An interface effect plays an important role in mediating the reaction rate due to the immiscibility between the products and the IL catalyst, and the products can be spontaneously separated. NMR analysis and DFT calculation suggest that a pair of cation and anion of [SO3H-BMIm][OTf] could form three strong H-bonds with an ether molecule, which catalyze the ether transformation via a cyclic oxonium intermediate. A series of O-heterocycles including tetrahydrofurans, tetrahydropyrans, morpholines and dioxane can be obtained from their corresponding ethers in excellent yields (e.g., >99 %). This work opens an efficient and metal-free way to produce O-heterocycles from aliphatic ethers.
Wang, Huan,Zhao, Yanfei,Zhang, Fengtao,Wu, Yunyan,Li, Ruipeng,Xiang, Junfeng,Wang, Zhenpeng,Han, Buxing,Liu, Zhimin
p. 11850 - 11855
(2020/05/16)

KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives
A new magnetic nanocatalyst (Fe3O4@KCC-1-npr-NH2) was synthesized directly through the reaction of Fe3O4@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.
Azizi, Sajjad,Shadjou, Nasrin,Hasanzadeh, Mohammad
(2019/11/22)

Synthesis of sulfonamides promoted by alkyl iodide via a hypervalent iodine intermediate
A new method for the preparation of sulfonamides from sodium sulfinates and amines is developed. A stoichiometric amount of m-chloroperbenzoic acid as oxidant and a catalytic amount of 1-iodopropane provides the corresponding sulfonamides in good yields under mild reaction conditions. In this protocol, 1-iodopropane is first oxidized by m-chloroperbenzoic acid into the corresponding hypervalent iodine intermediate iodosylpropane, which is highly unstable and decomposes at once to form hypoiodous acid. Then, the following reaction of the generated active hypoiodous acid with sodium sulfinates and amines results in the corresponding sulfonamides.
Zhou, Zhongshi,He, Xuehan
supporting information
p. 280 - 284
(2019/11/16)

Novel method for preparing oxygen heterocyclic compound through ionic liquid catalysis
The invention discloses a novel method for preparing an oxygen heterocyclic compound through ionic liquid catalysis. The ionic liquid catalytic system has the advantages of high efficiency, simplicity, mild reaction conditions, no metal participation, no by-product, simple separation and the like and can efficiently catalyze fatty diether metathesis cyclization to prepare an oxygen heterocyclic compound and has very high industrial application value.
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Paragraph 0097-0102

(2020/08/02)

Hypervalent Iodine Mediated Sulfonamide Synthesis
A new metal-free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group-transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram-scale. The reaction mechanism was investigated by ESI-MS and DFT calculations.
Poeira, Diogo L.,Macara, Jo?o,Faustino, Hélio,Coelho, Jaime A. S.,Gois, Pedro M. P.,Marques, M. Manuel B.
p. 2695 - 2701
(2019/04/08)

Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines
An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism.
Chung, Sohyun,Kim, Jinho
supporting information
p. 792 - 795
(2019/02/16)

Electrochemical anion pool synthesis of amides with concurrent benzyl ester synthesis
An electrosynthesis method for amide bond formation has been developed in an attempt to increase the atom economy for this class of reactions. This "anion pool" method electrochemically generates strong nucleophiles from amine substrates. The amine nucleophiles then react with acid anhydrides to generate amides, and the by-product from this reaction undergoes further chemical transformations to generate pharmaceutically relevant benzoic esters. These one-pot reactions are operationally simple, are performed at room temperature, and avoid rare transition metals and added bases. The amide synthesis is amenable to primary and secondary amines and a variety of anhydrides with yields up to 90% obtained. Atom economy and process mass index (PMI) values calculated for this procedure indicate that this process can be considered greener compared to traditional amide synthesis routes used by industry. Furthermore, this electrochemical approach showed unique selectivity when substrates that contained two inequivalent amine moieties were examined.
Mevan Dissanayake,Melville, Alex D.,Vannucci, Aaron K.
supporting information
p. 3165 - 3171
(2019/06/18)

Iron-Catalyzed Ring-Closing C?O/C?O Metathesis of Aliphatic Ethers
Among all metathesis reactions known to date in organic chemistry, the metathesis of multiple bonds such as alkenes and alkynes has evolved into one of the most powerful methods to construct molecular complexity. In contrast, metathesis reactions involving single bonds are scarce and far less developed, particularly in the context of synthetically valuable ring-closing reactions. Herein, we report an iron-catalyzed ring-closing metathesis of aliphatic ethers for the synthesis of substituted tetrahydropyrans and tetrahydrofurans, as well as morpholines and polycyclic ethers. This transformation is enabled by a simple iron catalyst and likely proceeds via cyclic oxonium intermediates.
Biberger, Tobias,Makai, Szabolcs,Lian, Zhong,Morandi, Bill
p. 6940 - 6944
(2018/05/14)

Synthesis of aromatic sulfonamides through a copper-catalyzed coupling of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-Chloroamines
A copper-catalyzed aminosulfonylation of aryldiazonium tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines is described. This coupling reaction provides an efficient and simple approach to a wide range of sulfonamides in moderate to good yields under mild conditions. Mechanistic investigation suggests that a radical process and transition-metal catalysis are merged in this tandem reaction.
Zhang, Feng,Zheng, Danqing,Lai, Lifang,Cheng, Jiang,Sun, Jiangtao,Wu, Jie
supporting information
p. 1167 - 1170
(2018/02/23)

PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
p. 2360 - 2364
(2018/05/24)

MANUFACTURING METHOD OF COMPOUND HAVING SULFONYL GROUP
The present invention relates to a method for manufacturing a compound having a sulfonyl group, which includes a step for reacting thiosulfonates in a solvent comprising nucleophilic bases with an electrophilic agent. Accordingly, the present invention can manufacture the compound having the sulfonyl group with a variety of structures with high efficiency and high yield through more simplified processes than conventional methods.COPYRIGHT KIPO 2018
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Paragraph 0187; 0188; 0190-0193

(2018/10/03)

Copper-Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides
Secondary or tertiary sulfinamides are prepared by copper-catalyzed transsulfinamidation of primary sulfinamides with O-benzoyl hydroxylamines. Subsequent oxidations of the resulting products lead to the corresponding sulfonamides. Treatment of N-aryl sulfinamides with O-benzoyl hydroxylamines under copper catalysis provides N-aryl sulfonimidamides.
Yu, Hao,Li, Zhen,Bolm, Carsten
p. 15602 - 15605
(2018/11/10)

Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers
By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-l-thyronine (3-T1) derivative was synthesized by this aryl migration procedure.
Chen, Huangguan,Han, Jianwei,Wang, Limin
supporting information
p. 12313 - 12317
(2018/09/10)

Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides
By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.
Bao, Xiaodong,Rong, Xiaona,Liu, Zhiguo,Gu, Yugui,Liang, Guang,Xia, Qinqin
supporting information
p. 2853 - 2858
(2018/06/25)

C5-Morpholinomethylation of: N 1-sulfonylcytosines by a one-pot microwave assisted Mannich reaction
A fast and efficient route for the introduction of a methylene bridged-amine (morpholinomethyl) functionality in the C5 position of the sulfonylated cytosine nucleobase has been developed. First, novel N1-sulfonylcytosine derivatives 3-6 were prepared by the condensation of silylated cytosine with selected sulfonyl chlorides. They were subsequently transformed to 5-morpholinomethyl-N1-sulfonylcytosine derivatives (8, 12-15) using microwave irradiation. As a result of cytosine ring opening in N1-tosylcytosine, depending on the reaction conditions, peculiar tosyl-urea derivative 9 has been isolated, which provided additional insight into the reaction pathway. The influence of the C5-substituent on the antiproliferative activity has been evaluated by performing the MTT test on U251, MCF-7 and MOLT-4 tumor cell-lines.
Mati?, Josipa,Nekola, Irena,Vi?njevac, Aleksandar,Kobeti?, Renata,Martin-Kleiner, Irena,Kralj, Marijeta,?ini?, Biserka
p. 2678 - 2687
(2018/04/27)

Eosin Y-Sensitized Photocatalytic Reaction of Tertiary Aliphatic Amines with Arenesulfonyl Chlorides under Visible-Light Irradiation
A mild, practical, and environmentally friendly route to vinyl sulfones and sulfonamides has been developed based on the reaction of aliphatic amines with arenesulfonyl chlorides in the presence of eosin Y as a photocatalyst under visible light. The method permits the selective formation of vinyl sulfones or sulfonamides, depending on the oxidation environment and solvent. A wide range of products were obtained in moderate to good yields under the optimized conditions.
Cai, Yuguo,Zhang, Ronghua,Sun, Deli,Xu, Song,Zhou, Qiguang
p. 1630 - 1635
(2017/08/11)

Preparation method for sulfonamide compound
The invention discloses a preparation method for a sulfonamide compound. The preparation method comprises the following steps: with NIS as an oxidizing agent and potassium tert-butoxide as a base, reacting formamide with sodium arylsulfinate in an organic solvent, and carrying out post-treatment after the reaction is completed so as to obtain the sulfonamide compound. The preparation method uses formamide and sodium arylsulfinate as substrates for synthesis of the sulfonamide compound; the raw materials for the reaction are cheap and easily available; and the preparation method is simple.
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Paragraph 0125; 0126; 0127; 0128; 0129; 0130

(2017/12/14)

Metal-free I2O5-mediated direct construction of sulfonamides from thiols and amines
A simple and convenient method has been developed for the construction of sulfonamides via I2O5-mediated sulfonylation of amines with arylthiols. The present protocol provides an attractive approach to sulfonamides in moderate to good yields from readily accessible and easy to handle starting materials under mild and metal-free conditions.
Zhu, Minghui,Wei, Wei,Yang, Daoshan,Cui, Huanhuan,Wang, Leilei,Meng, Guoqing,Wang, Hua
supporting information
p. 4789 - 4793
(2017/07/10)

Preparation method of sulfonamides compound
The invention discloses a reparation method of a sulfonamides compound. The preparation method includes: using thiophenol and amine which are simple and easy to get as raw materials; enabling the raw materials to be in direct oxidation coupling reaction under mediation of safe and stable iodine pentoxide to prepare sulfonamide. The preparation method has the advantages that reaction conditions are mild (60 DEG C), the raw materials are simple and easy to get and low in price, reaction environment is friendly, a substrate is wide in application range, and metal catalysts and harsh reaction conditions like low or high temperature and zero water and zero oxygen are not needed, so that metal pollution related to common synthesis methods is avoided; the preparation method further has the advantages of simple, convenient and safe operation, stable process condition and easiness in product purification and is suitable for large-scale production.
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Paragraph 0017; 0018

(2017/09/02)

One-Pot Bimetallic Pd/Cu-Catalyzed Synthesis of Sulfonamides from Boronic Acids, DABSO and O-Benzoyl Hydroxylamines
A practical and straightforward bimetallic Pd/Cu catalytic system has been developed. This system affords various sulfonamides in one pot from easy-to-handle and readily available boronic acids, sulfur dioxide surrogate DABSO and O-benzoyl hydroxylamines in high yields. Without additional ligands, the newly developed catalytic system revealed a broad substrate scope for both partners and tolerated a wide array of functional groups even at low catalyst loadings. Furthermore, based on control experiments, a plausible mechanism has been proposed, in which sodium sulfinate has been isolated and identified as the crucial intermediate for this transformation.
Zhu, Haibo,Shen, Yajing,Deng, Qinyue,Huang, Changyu,Tu, Tao
p. 706 - 712
(2017/03/22)

Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates
Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SO2, thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.
Shyam, Pranab K.,Jang, Hye-Young
p. 1761 - 1767
(2017/02/10)

Copper-Catalyzed Sulfonylation of Alkenes and Amines by Using Thiosulfonates as a Sulfonylating Agent
Synthetically and pharmaceutically useful vinyl sulfones and sulfonamides are synthesized by the direct coupling of thiosulfonates with alkenes and amines, respectively. Copper catalysts help to generate the sulfonyl group from thiosulfonates and to form the C(sp2)–S/N–S bonds of the organosulfur compounds. This paper discusses the scope of these reactions of aromatic and aliphatic thiosulfonates with alkenes and amines.
Shyam, Pranab K.,Son, Soobin,Jang, Hye-Young
p. 5025 - 5031
(2017/09/22)

DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents
Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.
Jones, Caroline S.,Bull, Steven D.,Williams, Jonathan M. J.
p. 8452 - 8456
(2016/09/28)

Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines
A novel, rapid, and environmentally-friendly protocol for the synthesis of sulfonamides using iodine as catalyst under solvent-free conditions is described. This method involves the oxidative coupling of sulfonyl hydrazides and amines in the presence of catalytic amount of iodine using TBHP as oxidant. This protocol does not require purification techniques such as column chromatography and recrystalization.
Parumala, Santosh Kumar Reddy,Peddinti, Rama Krishna
supporting information
p. 1232 - 1235
(2016/03/01)

Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines
An efficient electrochemical synthesis of sulfonamides (yields 56–98%) from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines was performed in an undivided cell with graphite anode and iron cathode in MeCN–H2O medium using halides as redox mediators and supporting electrolytes.
Terent'ev, Alexander O.,Mulina, Olga M.,Pirgach, Dmitry A.,Syroeshkin, Mikhail A.,Glinushkin, Alexey P.,Nikishin, Gennady I.
p. 538 - 539
(2016/12/02)

NH4I-Catalyzed Synthesis of Sulfonamides from Arylsufonylhydrazides and Amines
A novel and efficient approach to sulfonamides has been developed. Using TBHP as the oxidant and NH4I (20 mol%) as the catalyst, arylsulfonyl hydrazides reacted with amines to provide sulfonamides in moderate to good yields. Possible reaction pathway for the formation of the products was also discussed in this paper. Sulfonimides were synthesized through the oxidation coupling of arylsufonylhydrazides and amines by TBHP/NH4I system in moderate to good yields.
Yu, Hui,Zhang, Yonghao
supporting information
p. 359 - 362
(2016/04/26)

Electrosynthesis of Arylsulfonamides from Amines and Sodium Sulfinates Using H2O-NaI as the Electrolyte Solution at Room Temperature
With H2O as the solvent and NaI as the supporting electrolyte, a green and efficient electrochemical route has been developed to synthesize arylsulfonamides via I2electrogenerated in situ at a graphite anode to promote the reaction of sodium sulfinates with aromatic or aliphatic primary and secondary amines. The target products could be obtained in good to excellent yields at room temperature.
Zhang, Chen,Chen, Yibin,Yuan, Gaoqing
p. 1277 - 1282
(2016/12/27)

I2/TBHP Mediated C-N and C-H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction
A novel method toward synthesis of sulfonamides and β-arylsulfonyl enamines has been developed via I2/TBHP mediated C-N and C-H bond cleavage of tertiary amines, which features highly selective formation of two different target products depending on the reaction solvent. The experimental results reveal that H2O as the solvent could effectively achieve the C-N bond cleavage to produce sulfonamides due to H2O participating in the reaction process where H2O plays a dual role. Differing from H2O, organic solvents (such as dimethyl sulfoxide) could promote the C-H bond cleavage of tertiary amines to yield β-arylsulfonyl enamines.
Lai, Junyi,Chang, Liming,Yuan, Gaoqing
supporting information
p. 3194 - 3197
(2016/07/14)

Synthesis of sulfonamides: Via copper-catalyzed oxidative C-N bond cleavage of tertiary amines
A copper-catalyzed coupling reaction of sulfonyl chlorides with tertiary amines via the oxidative C-N bond cleavage of tertiary amines was developed. Sulfonamides were synthesized using this strategy in moderate to good yields. The reaction was applicable to various tertiary amines, as well as sulfonyl chlorides.
Ji, Jing,Liu, Zhengyi,Liu, Ping,Sun, Peipei
p. 7018 - 7023
(2016/07/30)

Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation
A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.
Deeming, Alex S.,Russell, Claire J.,Willis, Michael C.
supporting information
p. 747 - 750
(2016/02/27)

One-Pot Sulfonamide Synthesis Exploiting the Palladium-Catalyzed Sulfination of Aryl Iodides
Aryl ammonium sulfinates, conveniently prepared from aryl iodides and the sulfur dioxide surrogate DABSO, under the action of a palladium(0) catalyst, are transformed in a one-pot process to a variety of functionalized sulfonamides. The sulfinate to sulfonamide transformation is achieved by simple treatment with an aqueous solution of the relevant amine and sodium hypochlorite (bleach). A broad range of amines, including anilines, and amino acid derivatives, are combined efficiently with a variety of aryl iodides, leading to sulfonamides in high yields.
Flegeau, Emmanuel Ferrer,Harrison, Jack M.,Willis, Michael C.
supporting information
p. 101 - 105
(2015/12/26)

Sustainable synthesis of sulfonamides using supported ionic liquid phase catalyst containing Keggin-type anion
A silica-supported ionic liquid phase catalyst containing Keggin-type anion has been prepared by covalent grafting of ferrocene-tagged ionic liquid in a matrix of silica followed by anion metathesis reaction. This novel catalyst served as a robust heterogeneous catalyst for the synthesis of biologically active sulfonamides from 4-toluenesulfonyl chloride and amines. Additionally, recycling experiments showed that the catalyst could be reused five times.
Jagadale, Megha,Khanapure, Sharanabasappa,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
p. 125 - 131
(2016/02/14)

One-Pot Synthesis of Sulfonamides from Sodium Sulfinates and Amines via Sulfonyl Bromides
a new and convenient procedure has been developed for the preparation of sulfonamides from sodium sulfinates and amines with (n-C4H9)4NBr as bromine source and m-chloroperbenzoic acid as oxidant. This S-N bond formation reaction proceeds efficiently via sulfonyl bromides under neutral conditions to afford the corresponding sulfonamides in good yields at room temperature.
Wu, Sixue,Zhang, Yikun,Zhu, Min,Yan, Jie
p. 2699 - 2704
(2016/11/30)

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst
An efficient protocol for the synthesis of sulfonamides via the electrochemical oxidative amination of sodium sulfinates has been developed. The chemistry proceeds in a simple undivided cell employing a substoichiometric amount of NH4I that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required. A wide range of substrates, including aliphatic or aromatic secondary and primary amines, as well as aqueous ammonia, proved to be compatible with the protocol. Scale-up was possible, thereby demonstrating the practicality of the approach. The electrolytic process avoids the utilization of external oxidants or corrosive molecular iodine and therefore represents an environmentally benign means by which to achieve the transformation.
Jiang, Yang-Ye,Wang, Qing-Qing,Liang, Sen,Hu, Li-Ming,Little, R. Daniel,Zeng, Cheng-Chu
p. 4713 - 4719
(2016/07/06)

Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines
A new synthesis of sulfonamides has been developed via an iodine-catalyzed sulfonylation of amines with arylsulfonyl hydrazides. This metal-free strategy employs readily accessible and easy to handle starting materials, catalysts and oxidants, and can be easily conducted under mild conditions, providing a convenient access to a wide range of sulfonamides in moderate to excellent yields within a short reaction time.
Yotphan, Sirilata,Sumunnee, Ladawan,Beukeaw, Danupat,Buathongjan, Chonchanok,Reutrakul, Vichai
p. 590 - 597
(2016/01/12)

A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
Triphenylphosphine (PPh3)/N-chlorobenzotriazole (NCBT), and amine (primary and secondary aliphatic amines and also substituted anilines) in CH2Cl2 efficiently converted carboxylic acids, α-amino acids, and sulfonic acids to the corresponding amides and sulfonamides at room temperature. Good to excellent yields, inexpensive, and fast reaction conditions are the important features of this procedure.
Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
p. 1703 - 1714
(2015/09/15)

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature
A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is
Yang, Kai,Ke, Miaolin,Lin, Yuanguang,Song, Qiuling
p. 1395 - 1399
(2015/03/18)

Synthesis of sulfonamides via I2-mediated reaction of sodium sulfinates with amines in an aqueous medium at room temperature
An efficient I2-mediated approach for the synthesis of sulfonamides at room temperature using water as the solvent has been developed. This method for the synthesis of sulfonamides is quite convenient and environmentally friendly. In addition, the purification procedure of the desired products becomes very easy. This journal is
Pan, Xiaojun,Gao, Jian,Liu, Juan,Lai, Junyi,Jiang, Huanfeng,Yuan, Gaoqing
supporting information
p. 1400 - 1403
(2015/03/18)

Iodine-catalyzed oxidative amination of sodium sulfinates: A convenient approach to the synthesis of sulfonamides under mild conditions
The iodine-catalyzed oxidative amination of sodium sulfinates in the presence of sodium percarbonate as the oxidant has been developed. The reaction shows good substrate scope and tolerates a wide range of functionalities in both amine and sodium sulfinate substrates. Aliphatic amines, heteroaromatic amines and hydrochloride salts of amines canbe employed as the amine sources in this transformation. Mechanistic studies indicated that a radical pathway might be involved in the reaction process. This transition-metalfree protocol offers an alternative and convenient approach for a preparation of a series of sulfonamides in moderate to good yields under mild conditions.
Buathongjan, Chonchanok,Beukeaw, Danupat,Yotphan, Sirilata
p. 1575 - 1582
(2015/03/04)

Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature
By using O-benzoyl hydroxylamines as amine sources, the first convenient copper-catalyzed electrophilic amination of sodium sulfinates has been realized. Even with 2 mol% catalyst loading, the protocol provided an efficient and straightforward synthesis of a broad range of functional sulfonamides under ambient reaction conditions without an additional base and ligand. Based on the control experiments, a plausible mechanism was proposed.
Zhu, Haibo,Shen, Yajing,Deng, Qinyue,Tu, Tao
supporting information
p. 16573 - 16576
(2015/11/18)

Ultrasound-promoted green approach for the synthesis of sulfonamides using natural, stable and reusable Natrolite nanozeolite catalyst at room temperature
Natural Natrolite nanozeolite has been investigated as an efficient and reusable catalyst for the N-sulfonylation of amines under ultrasound irradiation at room temperature. Compared with traditional methods, the significant advantages for method are green solvent, milder and cleaner conditions, higher purity and yields, shorter reaction time, easier work-up procedure and the lower generation of waste or pollutions. The catalyst can be recovered and reused several times without significant loss of its catalytic activity.
Nasrollahzadeh, Mahmoud,Ehsani, Ali,Rostami-Vartouni, Akbar
p. 275 - 282
(2013/10/01)

Metal-free oxidative coupling of amines with sodium sulfinates: A mild access to sulfonamides
A practical and mild procedure for the preparation of sulfonamides through TBAI-catalyzed oxidative coupling of amines with sodium sulfinates using TBHP as an oxidant was presented. A variety of amines and sodium sulfinates could go through the transformation, without impacting the hydroxyl group. This journal is
Zhao, Jinwu,Xu, Jingxiu,Chen, Jiaxi,Wang, Xiaoqin,He, Minghua
p. 64698 - 64701
(2015/04/27)

Preparation of sulfonamides from N-silylamines
Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.
Naredla, Rajasekhar Reddy,Klumpp, Douglas A.
supporting information
p. 5945 - 5947
(2013/10/22)

Building a sulfonamide library by eco-friendly flow synthesis
A rapid and eco-friendly synthesis of a sulfonamide library under flow conditions is described. The study illustrates an efficient, safe, and easily scalable preparation of sulfonamides by use of a meso-reactor apparatus, thus demonstrating the impact of flow technologies within drug discovery. Waste minimization, employment of green media, and nontoxic reactants are achieved by the optimization of the flow setup and experimental protocol designed to sequentially synthesize primary, secondary, and tertiary sulfonamides. Isolation of the products involves only extraction and precipitation affording pure compounds in good to high yields without further purification for biological evaluation.
Gioiello, Antimo,Rosatelli, Emiliano,Teofrasti, Michela,Filipponi, Paolo,Pellicciari, Roberto
supporting information
p. 235 - 239
(2013/06/27)

Copper-catalyzed sulfonamides formation from sodium sulfinates and amines
A new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with 1 atm O2 or DMSO as the oxidant was described. This method provides efficient and robust synthesis of functional sulfonamides in good yields and excellent chemoselectivity. And detailed mechanistic studies showed that this transformation may go through a single electron transfer (SET) pathway.
Tang, Xiaodong,Huang, Liangbin,Qi, Chaorong,Wu, Xia,Wu, Wanqing,Jiang, Huanfeng
supporting information
p. 6102 - 6104
(2013/07/11)

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.
p. 4876 - 4878
(2011/12/05)