cas 2903-34-6, N-(4-CHLOROPHENYL)-P-TOLUENESULFONAMIDE

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An overview on the progress and development on the palladium catalyzed direct cyanation
Generation of the positive CN ion and the corresponding direct cyanation are both extremely important for cyanation of aromatic compounds. Hereby, we would like to report the simultaneous use of the new Pd nano-catalyst as well as the three types of the N-arylsulfonyl cyanamides (A, B and C) as potent reagents for the in situ generation of the positive CN ion for the direct cyanation of phenylboronic acids in acetonitrile at reflux conditions.
Heydari, Somayyeh,Habibi, Davood,Reza Faraji, Ali,keypour, Hassan,Mahmoudabadi, Masoumeh
(2020/10/02)

Immobilization of copper(II) into polyacrylonitrile fiber toward efficient and recyclable catalyst in Chan-Lam coupling reactions
A series of polyacrylonitrile fiber (PANF)-supported copper(II) catalysts were prepared through the immobilization of Cu(II) into prolinamide-modified PANF (PANPA-2F) and subsequently used for the synthesis of diverse N-arylimidazoles from arylboronic acids and imidazole. The prepared Cu(II)@PANPA-2Fs were well characterized by mechanical strength, FT-IR, XRD, XPS and SEM. Among them, CuCl2@PANPA-2F exhibited excellent catalytic performance, and its activity was significantly affected by the Cu loading. This catalytic system also displayed good activity in the synthesis of N-arylsulfonamides from arylboronic acids and tosyl azide. It was highly efficient in gram-scale reactions and could be reused five times. The advantages of low cost, easy preparation, good durability and facile recovery make the fiber catalyst attractive.
Zhang, Chenlu,Zhu, Hai,Gang, Kaiyue,Tao, Minli,Ma, Ning,Zhang, Wenqin
(2021/02/09)

Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides
The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.
Ahmadpoor, Fatemeh,Nasrollahzadeh, Mahmoud,Nezafat, Zahra,Pakzad, Khatereh
(2021/06/25)

Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium
A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.
Jiang, Xiaolan,Zhang, Kaili,Zhao, Rongrong,Bai, Die,Wang, Jinlong,Li, Binbin,Liu, Qixing,Zhou, Haifeng
supporting information

(2020/09/10)

Preparation method of sulfamide compound
The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of a sulfamide compound, wherein the structure of the sulfamide compound synthesizedby the method is characterized and confirmed by H NMR and C NMR. The method comprises the following steps: in an organic solvent, carrying out a reaction on an aryl diazonium salt, a sulfur dioxide solid complex and an aryl nitroso compound in the presence of a reducing agent under a heating condition, wherein the diazonium salt and the sulfur dioxide solid complex act to generate aryl sulfonyl free radicals, and then the aryl nitroso compound is attacked; and reducing the generated hydroxylamine to obtain the sulfamide compound. The preparation method of the compound has the advantages of mild conditions, simplicity, high efficiency, no need of catalysts, no need of pre-synthesis of sulfonyl chloride or sodium sulfonate reagents, wide substrate application range, strong functionalgroup compatibility, convenience in separation and purification, and excellent industrial and medicinal chemical application values.
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(2020/06/02)

Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under Metal-Free Conditions?
A metal-free reaction of nitrosoarenes, aryldiazonium tetrafluoroborates, and sulfur dioxide under mild conditions is developed, giving rise to sulfonamides in moderate to good yields. This transformation proceeds efficiently at room temperature in the presence of cyclohexa-1,4-diene with a broad reaction scope. Good functional group compatibility is observed, including cyano, halo, and ester. A plausible mechanism involving a radical process with the insertion of sulfur dioxide is proposed, and cyclohexa-1,4-diene serves as the reductant during the transformation.
Wang, Xuefeng,Lin, Yanmei,Liu, Jin-Biao,He, Fu-Sheng,Kuang, Yunyan,Wu, Jie
supporting information
p. 1098 - 1102
(2020/07/06)

Copper iodide nanoparticles-decorated porous polysulfonamide gel: As effective catalyst for decarboxylative synthesis of N-Arylsulfonamides
A porous cross-linked poly (ethyleneamine)-polysulfonamide (PEA-PSA) as a novel organic support system is synthesized in the presence of silica template by nanocasting technique. The paper demonstrates immobilization of CuI nanoparticles inside the pores (PEA-PSA?CuI) for the facile recovery and recycling of these nanoparticles. The presence of porous PEA-PSA and PEA-PSA?CuI nanocomposites was confirmed using FT-IR spectroscopy, FE-SEM, EDX, TGA, XRD, TEM, BET, XPS, WDX, 1H NMR, and ICP-OES techniques. The PEA-PSA?CuI along with Ag(I)/K2S2O8 was implemented as a reusable cooperative catalyst-oxidant system in the N-arylation of p-toluenesulfonamide with substituted carboxylic acids in mild condition. So, the novel decarboxylative cross-coupling catalyzed by copper and silver has been developed. Aromatic, secondary and tertiary aliphatic acids underwent high efficient decarboxylative processes with p-toluenesulfonamide to afford the corresponding products. This method provides a practical approach for the flexible synthesis of sulfonamides from the readily affordable substrates. The catalyst is highly reusable and efficient, especially in terms of time and yield of the desired product.
Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin,Rakhtshah, Jamshid,Yousefi Seyf, Jaber,Ali Arabian, Iman
(2020/01/22)

Facile Chan-Lam coupling using ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene
Ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of graphene followed by metallation with copper (I) iodide. The [GrFemImi]NHC@Cu complex has been characterized by fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), CP-MAS 13C NMR spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), energy dispersive X-ray (EDX) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET) surface area analysis and X-ray diffractometer (XRD) analysis. This novel complex served as a robust heterogeneous catalyst for the synthesis of bioactive N-aryl sulfonamides from variety of aryl boronic acids and sulfonyl azides in ethanol by Chan-Lam coupling. Recyclability experiments were executed successfully for six consecutive runs.
Gajare, Shivanand,Jagadale, Megha,Naikwade, Altafhusen,Bansode, Prakash,Rashinkar, Gajanan
(2019/04/08)

Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates
An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor
Seo, Jeong Hoon,Ko, Haye Min
supporting information
p. 671 - 674
(2018/01/19)

Halogen Bond Catalyzed Bromocarbocyclization
A halogen bond catalyzed bromo-carbocyclization of N-cinnamyl sulfonamides and O-cinnamyl phenyl ethers has been developed. N-methyl 4-iodopyridinium triflate is used as the halogen-bonding organocatalyst and the reaction is highly chemoselective. This report represents the first proof-of-concept for halogen-bonding organocatalyst-promoted electrophilic halogenation. Mechanistic study suggests the autocatalytic nature of this reaction.
Chan, Yuk-Cheung,Yeung, Ying-Yeung
supporting information
p. 3483 - 3487
(2018/02/28)

Differentiation of isomeric haloanilines by tosylation in combination with electrospray ionization mass spectrometry
Differentiation of the isomeric haloanilines still remains a challenging and?necessary?analytic task due to their identical retention time in chromatography and similar mass spectra. In this work, p-tosylation of haloanilines by reaction of haloanilines with p-toluenesulfonyl chloride resulted in the corresponding N-tosyl haloanilines. Fragmentation of protonated N-tosyl haloanilines in electrospray ionization tandem mass spectrometry (ESI-MS/MS) mainly resulted in tosyl cation, haloaniline radical cation, and halohydroxyaniline radical cation. The MS/MS of the three group isomeric derivatives showed significant difference in abundance distribution of these product ions, respectively. Theoretical calculations showed that the stability of the ion-neutral complex (INC) is a key factor influencing the relative intensity of the product ions. The three group isomeric derivatives were also separated by high performance liquid chromatograph (HPLC) at conventional conditions. p-Tosylation combined tandem MS (or HPLC) technique were carried out to realize the differentiation of isomeric haloanilines.
Wang, Shanshan,Cheng, Yuanyuan,Chen, Mengmeng,Jiang, Kezhi
p. 337 - 343
(2018/07/31)

Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium
A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.
Jiang, Jun,Zeng, Sheng,Chen, De,Cheng, Chaozhihui,Deng, Wei,Xiang, Jiannan
supporting information
p. 5016 - 5020
(2018/07/25)

Synthesis of N -Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature
A copper-catalyzed Chan-Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.
Ouyang, Banlai,Liu, Deming,Xia, Kejian,Zheng, Yanxia,Mei, Hongxin,Qiu, Guanyinsheng
supporting information
p. 111 - 115
(2017/12/27)

Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides
A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.
Ouyang, Banlai,Zheng, Yanxia,Liu, Yi,Liu, Fei,Yao, Juying,Peng, Yiyuan
p. 3694 - 3698
(2018/09/14)

NaI-Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants
A novel NaI-catalyzed oxidative amination of sodium sulfinates, employing both ethylene dibromide (EDB) and air as the oxidants, is described. EDB was first demonstrated to be a promising mild organic oxidant that in air, converted NaI into molecular iodine to promote the cross-coupling reactions of aromatic sodium sulfinates with amines to produce arylsulfonamides. Mechanistic studies indicated that a radical pathway might be involved in the reaction process.
Fu, Ying,Li, Quan-Zhou,Xu, Qin-Shan,Hügel, Helmut,Li, Ming-Peng,Du, Zhengyin
supporting information
p. 6966 - 6970
(2018/11/23)

Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
Ouyang, Yu-Qing,Yang, Zhen-Hua,Chen, Zhong-Hui,Zhao, Sheng-Yin
p. 771 - 778
(2017/04/06)

Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes
A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles.
Youn, So Won,Ko, Tae Yun,Jang, Young Ho
supporting information
p. 6636 - 6640
(2017/05/29)

An eco-friendly tandem tosylation/Ferrier N-glycosylation of amines catalyzed by Er(OTf)3 in 2-MeTHF
Er(OTf)3 in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-D-glucal and different nucleophiles affording good results in a short time.
Nardi, Monica,Cano, Natividad Herrera,De Nino, Antonio,Di Gioia, Maria Luisa,Maiuolo, Loredana,Oliverio, Manuela,Santiago, Ana,Sorrentino, Diletta,Procopio, Antonio
supporting information
p. 1721 - 1726
(2017/04/13)

CuI catalyzed sulfamidation of arylboronic acid using TsNBr2 at room temperature
An expeditious protocol for amidation arylboronic acid has been developed using TsNBr2 as the nitrogen source in presence of a CuI as catalyst. Various arylboronic acids could be transformed into corresponding N-arylsulfonamide derivatives within a very short time using CuI as catalyst in presence of DBU at room temperature.
Loukrakpam, Dineshwori Chanu,Phukan, Prodeep
supporting information
p. 4855 - 4858
(2017/11/29)

Triflic acid–catalyzed rearrangement of unalkylated benzene sulfonanilides
ABSTRACT: Previous work has demonstrated that alkylated benzene sulfonanilides undergo sulfuric acid (98%)–catalyzed rearrangement to alkylamino diaryl sulfones. Similar treatment of their unalkylated analogs typically leads only to hydrolysis. Surprisingly, when the unalkylated benzene sulfonanilides react with triflic acid, rearrangement to sulfones does occur.
Newcomer, Rebecca,McKee, James,Zanger, Murray
supporting information
p. 949 - 955
(2016/07/12)

An efficient practical tosylation of phenols, amines, and alcohols employing mild reagent [DMAPTs]+Cl?
Efficient exploration of [DMAPTs]+Cl?for base free and chromatography free preparation of sulfonate esters from phenols and alcohols and sulfonamides from amines was achieved in excellent yields. Majority of the phenols irrespective of their substituents electronic nature underwent tosylation nearly at same reaction rate with an average yield of 95%. For amines, ring activating substituents favors rapid sulfonylation while the ring deactivating substituents relatively lowers the rate of tosylation. Furthermore the reagent was employed for Chemoselective sulfonylation as well as solvent free tosylation of phenols and amines.
Dhonthulachitty, Chiranjeevi,Kothakapu, Sridhar Reddy,Neella, Chandra Kiran
supporting information
p. 4620 - 4623
(2016/09/23)

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)

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)

Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes
A palladium-catalyzed construction for N-arylsulfonamide from nitroarenes and arylsulfonyl hydrazides is developed. In this protocol, abundant and stable nitroarenes serve as the nitrogen sources by in situ reduction reaction of hydrogen released from arylsulfonyl hydrazides. No external oxidants or reductants are needed for this kind of transformation.
Zhao, Feng,Li, Bin,Huang, Huawen,Deng, Guo-Jun
p. 13010 - 13013
(2016/02/12)

A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling reaction of sulfonyl azides with arylboronic acids leading to: N -arylsulfonamides
A heterogeneous Chan-Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an l-proline-functionalized MCM-41-immobilized copper(i) complex [MCM-41-l-proline-CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily available and inexpensive reagents, and recovered by simple filtration of the reaction solution and recycled at least 8 times without any decreases in activity.
You, Chongren,Yao, Fang,Yan, Tao,Cai, Mingzhong
p. 43605 - 43612
(2016/05/24)

Iron-catalyzed N -arylsulfonamide formation through directly using nitroarenes as nitrogen sources
One-step, catalytic synthesis of N-arylsulfonamides via the construction of N-S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N-S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.
Zhang, Weixi,Xie, Junyao,Rao, Bin,Luo, Meiming
p. 3504 - 3511
(2015/04/14)

Tosyl oxygen transfer and ion-neutral complex mediated electron transfer in the gas-phase fragmentation of the protonated N-phenyl p-toluenesulfonamides
In this work, an interesting oxygen transfer reaction in the gas phase dissociation of N-phenyl p-toluenesulfonamides has been explored by combination of the ESI-MS techniques and theoretical calculations. The protonated molecules underwent dissociation reactions, upon collisional activation, to give the [tosyl cation/aniline] ion-neutral complex (INC), in which the coupling reactions subsequently occurred to afford an ionic species of toluenesulfinate. The subsequent reactions of the toluenesulfinate species resulted in generation of the protonated 6-iminocyclohexa- 2,4-dienone or the 2-aminophenol radical cation, via cleavage of the SO bond. The above processes involved the tosyl oxygen transfer, and calculation results indicated that both the ortho- and the para- positions at the aniline ring are favorite for the tosyl oxygen transfer, and formation of radical cation involved an INC mediated electron transfer. The isomeric N-methylphenyl p-toluenesulfonamides behaved significant difference in the CID-MS spectra, indicating that the three isomers can be distinguished by ESI-MS.
Wang, Shanshan,Guo, Cheng,Zhang, Ningwen,Wu, Yanqing,Zhang, Huarong,Jiang, Kezhi
p. 6 - 12
(2015/01/30)

Tosyl oxygen transfer and ion-neutral complex mediated electron transfer in the gas-phase fragmentation of the protonated N-phenyl p-toluenesulfonamides
In this work, an interesting oxygen transfer reaction in the gas phase dissociation of N-phenyl p-toluenesulfonamides has been explored by combination of the ESI-MS techniques and theoretical calculations. The protonated molecules underwent dissociation reactions, upon collisional activation, to give the [tosyl cation/aniline] ion-neutral complex (INC), in which the coupling reactions subsequently occurred to afford an ionic species of toluenesulfinate. The subsequent reactions of the toluenesulfinate species resulted in generation of the protonated 6-iminocyclohexa- 2,4-dienone or the 2-aminophenol radical cation, via cleavage of the SO bond. The above processes involved the tosyl oxygen transfer, and calculation results indicated that both the ortho- and the para- positions at the aniline ring are favorite for the tosyl oxygen transfer, and formation of radical cation involved an INC mediated electron transfer. The isomeric N-methylphenyl p-toluenesulfonamides behaved significant difference in the CID-MS spectra, indicating that the three isomers can be distinguished by ESI-MS.
Wang, Shanshan,Guo, Cheng,Zhang, Ningwen,Wu, Yanqing,Zhang, Huarong,Jiang, Kezhi
p. 6 - 12
(2015/02/19)

Palladium-Catalyzed Allylic Amination of Homoallylic Alcohols with Amines via Carbon-Carbon Bond Cleavage
An efficient approach for palladium(II) acetate catalyzed allylic amination of homoallylic alcohols with various amines via sequential retro-allylation and amination was developed, which afforded the corresponding allylic amines in up to 98% yield.
Sun, Gui-Jun,Wang, Yong,Kang, Qiang
supporting information
p. 2931 - 2936
(2015/09/28)

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)

Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
p. 8010 - 8019
(2015/03/18)

Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation
An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or ‘N-pseudoglycals’ in good yields (64–98%). High α-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions.
Reddy, Thurpu Raghavender,Chittela, Sravanthi,Kashyap, Sudhir
supporting information
p. 9224 - 9229
(2017/09/08)

Practical and metal-free electrophilic aromatic halogenation by interhalogen compounds generated in situ from N-halosuccinimide and catalytic TMSCL
Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds. Georg Thieme Verlag Stuttgart New York.
Maibunkaew, Tapanee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Bunrit, Anon,Ruchirawat, Somsak
supporting information
p. 1769 - 1775
(2014/08/05)

Copper-catalyzed Chan-Lam Coupling between Sulfonyl Azides and Boronic acids at room temperature
A mild and efficient method for the synthesis of N-arylsulfonamides in the presence of 10 mol % of CuCl is demonstrated. The reaction proceeds readily at room temperature in an open flask using a variety of sulfonyl azides and boronic acids without any base, ligand, or additive.
Moon, Soo-Yeon,Nam, Jungsoo,Rathwell, Kris,Kim, Won-Suk
supporting information
p. 338 - 341
(2014/04/03)

Natural Indian Natrolite zeolite-supported Cu nanoparticles: A new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions
We report here on the preparation of primary sulfonamides and efficient, easily recoverable and reusable copper nanoparticles supported on natural Indian Natrolite zeolite as a catalyst for arylation of sulfonamides with arylboronic acids in water. The catalyst was characterized using the powder XRD, SEM, EDS and FT-IR spectroscopy. The significant advantages of this methodology are high yields, elimination of organic solvents, and simple work-up procedure. The catalyst was easily isolated from the reaction mixture and reused with no significant loss in its activity.
Azarifar, Davood,Soleimanei, Fatemeh
p. 12119 - 12126
(2014/03/21)

Fabrication, characterization and application of nanopolymer supported copper (II) complex as an effective and reusable catalyst for the CN bond cross-coupling reaction of sulfonamides with arylboronic acids in water under aerobic conditions
This paper reports on the synthesis and use of nanopolymer supported copper (II) complex, as separable catalysts for N-arylation of sulfonamides with arylboronic acids in water. This method has the advantages of high yields, elimination of homogeneous cat
Nasrollahzadeh, Mahmoud,Rostami-Vartooni, Akbar,Ehsani, Ali,Moghadam, Majid
p. 123 - 129
(2014/04/03)

Copper-catalyzed ortho-halogenation of protected anilines
A practical Cu-catalyzed direct ortho-halogenation of anilines under aerobic conditions has been developed. The reaction shows typically excellent mono-substitution selectivity, high ortho-regiocontrol and large functional group tolerance.
Urones, Beatriz,Martinez, Angel Manu,Rodriguez, Nuria,Arrayas, Ramon Gomez,Carretero, Juan C.
p. 11044 - 11046
(2013/11/19)

Combustion-derived CdO nanopowder as a heterogeneous basic catalyst for efficient synthesis of sulfonamides from aromatic amines using p-toluenesulfonyl chloride
A simple and rapid synthesis of CdO nanopowder via the solution combustion route employing l-(+)-tartaric acid as a fuel is reported for the first time. The catalyst was characterized by PXRD, SEM, TEM, BET surface area measurement, basic site measurement from back titration and FTIR. Combustion derived CdO nanopowder acts as a catalyst in the sulfonylation of amines with p-toluenesulfonyl chloride to obtain sulfonamides in excellent yield (85-95 %) and high purity under mild reaction conditions. CdO nanopowder has been found to be an efficient catalyst requiring a shorter reaction time (10-30 min) to obtain sulfonamide when compared with the commercial CdO powder requiring 2 h under similar conditions. The catalyst can be recovered and reused four times without any significant loss of catalytic activity. Potential role of CdO nanopowder in the synthesis of sulfonamides and its mechanism is proposed.
Anandakumar, Belladamadu Siddappa,Madhusudana Reddy, Muthukur Bhojegowd,Thipperudraiah, Kumarappa Veerappa,Pasha, Mohamed Afzal,Chandrappa, Gujjarahalli Thimmanna
p. 135 - 144
(2013/06/04)

Chemoselective nitration of aromatic sulfonamides with tert-butyl nitrite
A methodology for the efficient conversion of aromatic sulfonamides into their mono-nitro derivatives using tert-butyl nitrite is reported. The reaction exhibits a high degree of chemoselectivity for sulfonamide functionalized aryl systems, even in the presence of other sensitive or potentially reactive functionalities.
Kilpatrick, Brenden,Heller, Markus,Arns, Steve
supporting information
p. 514 - 516
(2013/02/25)

Synthesis of Oxindoles through the gold-catalyzed oxidation of N-arylynamides
α-Oxo gold carbenoids generated by the oxidation of N-arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N-oxide works as the oxidant, ligand, and base in this transformation. Copyright
Yang, Liu-Qing,Wang, Kai-Bing,Li, Chuan-Ying
supporting information
p. 2775 - 2779
(2013/06/27)

Tetrahydroquinolines by lewis acid-promoted friedel-crafts cyclizations
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Bunce, Richard A.,Cain, Nicholas R.,Cooper, John G.
p. 28 - 43
(2013/03/14)

Efficient manganese/copper bimetallic catalyst for N-arylation of amides and sulfonamides under mild conditions in water
An efficient and mild method using a bimetallic MnF2/CuI catalyst at 60 °C in water was developed for the N-arylation of amides and sulfonamides with aryl halides. A variety of functionalized amides and sulfonamides were coupled with different substituted aryl halides to afford the corresponding N-arylated products in good to excellent yields (up to 97 %). An efficient method using a bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane as the ligand has been developed for the cross-coupling of benzamides and sulfonamides with differently substituted aryl iodides in water. The corresponding N-arylated products were obtained in good to excellent yields (up to 97 %) under the catalytic conditions. Copyright
Teo, Yong-Chua,Yong, Fui-Fong,Ithnin, Idzham Khalid,Yio, Siew-Hui Trionna,Lin, Zhiyin
supporting information
p. 515 - 524
(2013/02/26)

Ionic liquid-supported synthesis of sulfonamides and carboxamides
An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.
Muthayala, Manoj Kumar,Chhikara, Bhupender S.,Parang, Keykavous,Kumar, Anil
experimental part
p. 60 - 65
(2012/02/04)

A green, catalyst-free method for the synthesis of sulfonamides and sulfonylazides
A novel, green method for the efficient synthesis of sulfonamide and sulfonylazide derivatives by the reaction of sulfonyl chlorides with amines or sodium azide under catalyst-free conditions has been developed. The reactions proceed with high yields and excellent selectivities in short reaction times. Copyright Taylor & Francis Group, LLC.
Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Golshani, Tayebeh
experimental part
p. 140 - 148
(2011/04/22)

Cs2CO3 catalyzed rapid and efficient conversion of amines into sulfonamides; Alcohols and phenols into sulfonic esters
A simple and efficient method has been developed for the sulfonylation of several amines, alcohols, and phenols by p-toluenesulphonylchloride (p-TsCl) in the presence of catalytic amount of Cs2CO3 at 25C to obtain sulfonamides and sulfonic esters in very good yields. Cs2CO3 has been found to be highly efficient catalyst. Taylor & Francis Group, LLC.
Reddy, M. B. Madhusudana,Pasha
experimental part
p. 1867 - 1875
(2011/10/11)

Efficient ligand-free, copper-catalyzed N-arylation of sulfonamides
An efficient and convenient protocol has been developed for the N-arylation of sulfonamides with differently substituted aryl iodides using ligand-free copper iodide to afford the arylated products in good to excellent yields (up to 91%). Georg Thieme Verlag Stuttgart.
Teo, Yong-Chua,Yong, Fui-Fong
supporting information; experimental part
p. 837 - 843
(2011/06/21)

A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
Cupric Oxide efficiently catalyzed the synthesis of sulfonamides and sulfonic esters. This method has been applied to a variety of substrates including nucleophilic and sterically-hindered amines, alcohols and phenols with excellent yields of sulfonamides and sulfonic esters. The remarkable selectivity under mild and neutral conditions of this commercially available inexpensive catalyst is an attractive feature of this method.
Meshram,Patil, Vishvanath D.
scheme or table
p. 1117 - 1121
(2009/05/27)

Cu(OAc)2-catalyzed N-arylation of sulfonamides with arylboronic acids or trimethoxy(phenyl)silane
Cu(OAc)2-catalyzed C-N bond-formation reaction of sulfonamides with organoboronic acids or trimethoxy(phenyl)silane was achieved in the presence of 20mol% of Cu(OAc)2, providing N-arylation products with yields ranging from moderate to good.
Pan, Changduo,Cheng, Jiang,Wu, Huayue,Ding, Jinchang,Liu, Miaochang
experimental part
p. 2082 - 2092
(2009/10/17)

An efficient method for the synthesis of N-acylsulfonamides: One-pot sulfonylation and acylation of primary arylamines under solvent-free conditions
The preparation of N-acylsulfonamides is described using primary amines, arylsulfonyl chlorides and acyl chlorides. Reaction of primary aryl amines with arylsulfonyl chlorides in the presence of NaHCO3 produced N-arylsulfonamides, which reacted in situ with benzoyl chloride furnishing the corresponding N-benzoyl-N-arylsulfonamides in 72-96% yields. Accordingly, 4-nitrobenzoyl chloride and 3,5-dinitrobenzoyl chloride were used as acylating agents. All the reactions were carried out under solvent-free conditions at room temperature and the products were isolated after simple work-up in high yields and purity.
Massah, Ahmad R.,Azadi, Davood,Aliyan, Hamid,Momeni, Ahmad R.,Naghash, Hamid Javaherian,Kazemi, Foad
experimental part
p. 233 - 240
(2009/05/26)

Identification of novel glycine sulfonamide antagonists for the EP1 receptor
A high-throughput screen targeting the EP1 receptor identified non-acidic glycine sulfonamide derivative 2a with a pKi of 6.2. Analogue synthesis allowed a thorough investigation of the structure-activity relationship (SAR) and led to a 100-fold increase in recombinant potency.
McKeown, Stephen C.,Hall, Adrian,Blunt, Richard,Brown, Susan H.,Chessell, Iain P.,Chowdhury, Anita,Giblin, Gerard M.P.,Healy, Mark P.,Johnson, Matthew R.,Lorthioir, Olivier,Michel, Anton D.,Naylor, Alan,Lewell, Xiao,Roman, Shilina,Watson, Stephen P.,Winchester, Wendy J.,Wilson, Richard J.
p. 1750 - 1754
(2007/10/03)