- Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans
-
A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance. (Figure presented.).
- Chen, Xingyu,Lu, Sixian,Deng, Ping,Chang, Xiaoqiang,Zhao, Yifan,Ma, Yue,Zhang, Dong,Xia, Fei,Yang, Lan,Wang, Jigang,Sun, Peng
-
supporting information
p. 94 - 102
(2021/10/05)
-
- Identification of a Nitrenoid Reductive Elimination Pathway in Nickel-Catalyzed C-N Cross-Coupling
-
Whereas the (bisphosphine)Ni-catalyzed C-N cross-coupling of (hetero)aryl (pseudo)halides with NH nucleophiles represents a useful method for the synthesis of (hetero)anilines, our mechanistic understanding of such cross-couplings is incomplete, especially regarding key C-N reductive elimination steps that are often invoked as turnover-limiting. In this combined experimental and computational study, we provide evidence of a bifurcated C-N reductive elimination pathway for cross-couplings of tBuNH2 and (aryl′)SO2NH2 employing (L1)Ni(aryl)Cl as the precatalyst (L1 = PhPAd-DalPhos). In contrast with direct C-N reductive elimination that proceeds from the nickel alkylamido complex (L1)Ni(aryl)(NHtBu), we provide evidence of a previously undocumented base-promoted pathway involving deprotonation of the nickel sulfonamido complex (L1)Ni(aryl)(NHSO2(aryl′)) to give the anionic nickel nitrenoid species [(L1)Ni(aryl)(NSO2(aryl′))]-, from which C-N reductive elimination occurs preferentially.
- Dudra, Samantha L.,Ferguson, Michael J.,Johnson, Erin R.,McGuire, Ryan T.,Simon, Connor M.,Stradiotto, Mark
-
p. 1475 - 1480
(2022/02/07)
-
- Method for synthesizing P-chloroO-toluidine
-
The invention discloses a method for synthesizing p-chloroo-toluidine, which comprises the following steps: synthesizing o-toluidine and a protective agent in an organic solvent to obtain an amino-protected intermediate. The amino protected intermediate is added into hydrochloric acid, an oxidant is added for chlorination reaction, and a chlorination product is obtained. The chlorinated product is removed and the amino protecting group is removed to give p-chloroo-toluidine. The method for synthesizing p-chloroo-toluidine provided by the invention is high in yield, simple to operate, less in three wastes, high in product content and good in quality, and can be suitable for industrial mass production.
- -
-
Paragraph 0090-0091
(2021/10/05)
-
- Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation
-
The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.
- Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.
-
supporting information
(2021/11/09)
-
- 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
-
-
- 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
-
-
- Synthetic method for 2-amino-4'-fluoro-benzophenone
-
The invention discloses a synthetic method for 2-amino-4'-fluoro-benzophenone. The method comprises the following steps: subjecting o-toluidine and tosyl chloride to an amidation reaction to obtain 4-methyl-N-(2-methylphenyl) benzenesulfonamide; then performing chlorination by a chlorine gas, producing a Friedel-Crafts reaction with fluorobenzene, and obtaining N-(2-(4-fluorobenzoyl)phenyl)-4-toluenesulfonamide; and finally obtaining the 2-amino-4'-fluoro-benzophenone by deprotection of concentrated sulfuric acid. The synthetic method is cheap and easily available in starting material, is lowin cost, is convenient to operate, is suitable for industrial production, is green and environmentally friendly in synthetic route, and is high in yield, and the purity of the 2-amino-4'-fluoro-benzophenone obtained by preparation is good.
- -
-
Paragraph 0050-0052; 0055-0057; 0060-0062; 0065-0067; 0071
(2019/04/17)
-
- Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones
-
An alternative approach with eco-friendliness and high efficiency for the preparation of unsymmetrical diaryl sulfones has been developed. The strategy takes advantage of the reaction of sulfonyl hydrazides with quinone imine ketals catalyzed by DABCO (triethylenediamine) in ethanol. This transformation proceeds via a Lewis base promoted, direct 1,4-conjugate addition/sulfonylation/alcohol elimination reaction sequence. The protocol provides an efficient approach to access an array of diverse unsymmetrical diaryl and heterodiaryl sulfones, aryl alkyl sulfones and aryl vinyl sulfones in good to excellent yields.
- Liu, Teng,Liu, Jianjun,Shen, Xianfu,Xu, Jianbin,Nian, Beifang,He, Ni,Zeng, Shunqun,Cheng, Feixiang
-
p. 1365 - 1376
(2019/03/08)
-
- Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization
-
N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.
- Kikkawa, Shoko,Masu, Hyuma,Katagiri, Kosuke,Okayasu, Misaki,Yamaguchi, Kentaro,Danjo, Hiroshi,Kawahata, Masatoshi,Tominaga, Masahide,Sei, Yoshihisa,Hikawa, Hidemasa,Azumaya, Isao
-
p. 2936 - 2946
(2019/05/10)
-
- Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
-
A simple copper-catalyzed redox coupling of sodium sulfinates and nitroarenes is described. In this process, abundant and stable nitroarenes serve as both the nitrogen sources and oxidants, and sodium sulfinates act as both reactants and reductants. A variety of aromatic sulfonamides were obtained in moderate to good yields with broad substrate scope. No external additive is employed for this kind of transformation.
- Liu, Saiwen,Chen, Ru,Zhang, Jin
-
-
- Selective C(sp2)-H Amination Catalyzed by High-Valent Cobalt(III)/(IV)-bpy Complex Immobilized on Silica Nanoparticles
-
High-valent cobaltIV-bpy complex stabilized in silica matrix was detected as catalytically active form and intermediate in cobalt-mediated oxidative C?H/NH cross-coupling reaction. These CoIV species prepared by electrooxidation of CoIII(bpy)3-doped silica nanoparticles (SNs) at relatively low anodic potentials have demonstrated high catalytic activity. Both size and architecture of the SNs are highlighted as the factors beyond the complex structure affecting its oxidation potential and catalytic efficiency. The factors have been optimized for the catalyst with high efficiency, easy separation and reusability for 7 times at least. The optimal nanocatalyst (1 mol%) provides 100 % conversion of reactants in a single step of ligand-directed coupling of H2NTs with arenes under electrochemical regeneration conditions. The results emphasize both synthetic route for efficient embedding of CoIII(bpy)3 into silica support and the electrochemical generation of CoIV complexes as a facile route for developing the efficient nanocatalyst of oxidative functionalization. The observed reactivity has the potential in development of Co-catalyzed coupling reactions.
- Budnikova, Yulia,Bochkova, Olga,Khrizanforov, Mikhail,Nizameev, Irek,Kholin, Kirill,Gryaznova, Tatyana,Laskin, Artem,Dudkina, Yulia,Strekalova, Sofia,Fedorenko, Svetlana,Kononov, Aleksandr,Mustafina, Asia
-
p. 5615 - 5624
(2019/11/11)
-
- A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides
-
Gold-catalysed oxidative cyclisation reactions of ynamides offer great promise in γ-lactam synthesis but are limited by preferential over-oxidation to form α-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused γ-lactams on changing the ynamide N-substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3-aryl indoles and cyclohepta[c]pyrrol-1-one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.
- Sánchez-Cantalejo, Fernando,Priest, Joshua D.,Davies, Paul W.
-
supporting information
p. 17215 - 17219
(2018/11/10)
-
- 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)
-
- NOVEL BENZO [...] DERIVATIVES AND THEIR MEDICAL USE
-
One objective of the present invention is to provide a compound having V2 receptor agonist effect. The pharmaceutical composition of this invention uses a compound expressed by the following general formula (I) or its pharmacologically acceptable salt as an active ingredient, wherein, R1 represents the following formula: wherein, A represents a lower alkylene group or the like which may be substituted with a lower alkyl group; R6 represents a hydrogen atom or the like; R7 represents a hydroxyl group, an aromatic heterocyclic group which may be substituted with a lower alkyl group, amine methyl acyl or the like; R2 represents a hydrogen atom or a lower alkyl group; R3 represents a lower alkyl group which may be substituted with 1 to 3 fluorine atoms or a halogen atom; R4 represents 5-membered aromatic monocyclic heterocyclic group, or 5-membered non-aromatic monocyclic heterocyclic group or the like, wherein the heterocyclic group contains at least one nitrogen atom, and may be substituted with a lower alkyl group; R 5 represents a lower alkyl group or a halogen atom or the like.
- -
-
Page/Page column 32
(2019/04/26)
-
- 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)
-
- 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)
-
- 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)
-
- Discovery, Optimization, and Biological Evaluation of Sulfonamidoacetamides as an Inducer of Axon Regeneration
-
Axon regeneration after injury in the central nervous system is hampered in part because if an age-dependent decline in the intrinsic axon growth potential, and one of the strategies to stimulate axon growth in injured neurons involves pharmacological manipulation of implicated signaling pathways. Here we report phenotypic cell-based screen of chemical libraries and structure-activity-guided optimization that resulted in the identification of compound 7p which promotes neurite outgrowth of cultured primary neurons derived from the hippocampus, cerebral cortex, and retina. In an animal model of optic nerve injury, compound 7p was shown to induce growth of GAP-43 positive axons, indicating that the in vitro neurite outgrowth activity of compound 7p translates into stimulation of axon regeneration in vivo. Further optimization of compound 7p and elucidation of the mechanisms by which it elicits axon regeneration in vivo will provide a rational basis for future efforts to enhance treatment strategies.
- Ku, Jin-Mo,Park, Kyuhee,Lee, Jung Hun,Cho, Kyong Jin,Nam, Yeon-Ju,Jeong, Dae-Youn,Kim, Yu-Han,Kwon, Soonjung,Park, Ju-Young,Yang, Jungeun,Nam, Tae-Gyu,Yoon, Sung-Hwa,Ahn, Sangmee,Choi, Yongmun
-
p. 4676 - 4687
(2016/06/13)
-
- 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)
-
- 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 nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions
-
An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)2 in PEG-400 under air. Aryl bromides and triflates react at 35°C, while aryl chlorides require heating to 50°C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.
- Khalaj, Mehdi,Ghazanfarpour-Darjani, Majid,Talei Bavil Olyai, Mohamad Reza,Shamami, Sakineh Faraji
-
p. 211 - 221
(2016/03/30)
-
- A convenient and benign synthesis of sulphonamides in PEG-400
-
A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.
- Das, Pranab Jyoti,Sarmah, Bhaskar
-
p. 189 - 191
(2015/02/19)
-
- 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
-
-
- 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
-
-
- Nickel-catalyzed monoarylation of ammonia
-
Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.
- Borzenko, Andrey,Rotta-Loria, Nicolas L.,Macqueen, Preston M.,Lavoie, Christopher M.,McDonald, Robert,Stradiotto, Mark
-
supporting information
p. 3773 - 3777
(2015/03/18)
-
- Transition-metal-free direct amination of simple arenes with sulfonyl azides
-
A metal-free green protocol has been developed for amination of simple arenes using arylsulfonyl azides via a nitrene transfer process under solvent free conditions at 130 °C releasing N2 gas as the sole by-product.
- Wang, Lianggui,Borah, Arun Jyoti,Yan, Guobing
-
supporting information
p. 1353 - 1355
(2015/03/04)
-
- 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)
-
- 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 arylation of aryl sulfonamides with cyclohexanones
-
Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of aryl sulfonamides with cyclohexanones. Various N-aryl sulfonamides were selectively obtained in good yields using molecular oxygen as oxidant. The reaction tolerated a wide range of functionalities.
- Cao, Xiangxiang,Bai, Yang,Xie, Yanjun,Deng, Guo-Jun
-
-
- 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)
-
- Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI
-
The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II and human serum isozyme VI, with a series of tosylited aromatic amine derivatives was investigated. The KI ranges of compounds 1-14 and acetazolamide against hCA I ranged between 1.130 and- 448.2 μM, against hCA II between 0.103 and- 14.3 μM, and against hCA VI ranged between 0.340 and- 42.39 μM. Tosylited aromatic amine derivatives are thus interesting hCA I, II and VI inhibitors, and might be used as leads for generating enzyme inhibitors eventually targeting other isoforms which have not been assayed yet for their interactions with such agents.
- Alp, Cemalettin,?zsoy, ?eyda,Alp, Nurdan Alcan,Erdem, Deryanur,Gültekin, Mehmet Serdar,Küfrevio?lu, ?mer Irfan,?entürk, Murat,Supuran, Claudiu T.
-
p. 818 - 824
(2013/02/23)
-
- Half-sandwich scorpionates as nitrene transfer catalysts
-
Scorpionate complexes of the middle to late 3d transition metals [(L)M(NCMe)3](BF4)n (M = Mn, Fe, Co, Ni: 1 M, L = tris(3,5-dimethylpyrazol-1-yl)methane, TpmMe,Me, n = 2; 2M, L = tris(3-phenylpyrazol-1-yl)methane, TpmPh, n = 2; 3M except 3Mn, L = hydrotris(3,5-dimethylpyrazol-1-yl) borate, [TpMe,Me]-, n = 1; 4M, L = hydrotris(3-phenyl-5-methylpyrazol-1-yl)borate, [TpPh,Me] -, n = 1) were examined as catalysts for styrene aziridination and THF amination using phenyl-N-tosyliodinane as a nitrene donor. [(Tpm Me,Me)Fe(NCMe)3](BF4)2 (1 Fe) was identified as the most active catalyst, giving nearly quantitative nitrene transfer yields at 5 mol % loadings. The reactivity of 1Fe with a wider range of organic substrates was also explored, and a striking observation was strong selectivity for aromatic rather than benzylic amination for alkylaromatic substrates.
- Liang, Shengwen,Jensen, Michael P.
-
p. 8055 - 8058
(2013/02/22)
-
- 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)
-
- Coupling of ortho-substituted aryl chlorides with bulky amides
-
Voluminous amides were coupled with deactivated, sterically hindered aryl chlorides in excellent yields providing products, which have not been efficiently accessible by transition metal catalysis so far. Application of an unsymmetric bisphosphine ligand was critical for the high catalytic activity.
- Falk, Florian C.,Froehlich, Roland,Paradies, Jan
-
supporting information; experimental part
p. 11095 - 11097
(2011/11/07)
-
- A general method for palladium-catalyzed reactions of primary sulfonamides with aryl nonaflates
-
A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO 4 in tert-amyl alcohol was found to be the optimal base-solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.
- Shekhar, Shashank,Dunn, Travis B.,Kotecki, Brian J.,Montavon, Donna K.,Cullen, Steven C.
-
p. 4552 - 4563
(2011/07/31)
-
- Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3
-
An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.
- Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
-
experimental part
p. 143 - 148
(2010/11/16)
-
- 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)
-
- 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)
-
- β-cyclodextrin-catalyzed monosulfonylation of amines and amino acids in water
-
A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.
- Sridhar,Srinivas,Kumar, V. Pavan,Narender,Rao, K. Rama
-
p. 1873 - 1876
(2008/09/16)
-
- 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)
-
- Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands
-
A highly general, convenient, and inexpensive catalyst system was developed for the N-arylation of sulfonamides with aryl iodides or bromides by using 5-20 mol % of CuI as catalyst, 20 mol % of N-methylglycine (for aryl iodides) or N,N-dimethylglycine (for aryl bromides) as ligand, and K3PO 4 as base.
- Deng, Wei,Liu, Lei,Zhang, Chen,Liu, Min,Guo, Qing-Xiang
-
p. 7295 - 7298
(2007/10/03)
-
- A mild and simple synthesis of N-aryl substituted toluenesulfamides under solvent-free conditions
-
In this paper, a series of N-aryl substituted toluenesulfamides were synthesised by grinding under solvent-free conditions at room temperature. The yields were excellent (88%-97%), and the process is simple.
- Zhao, Na,Wang, Yu-Lu
-
p. 366 - 367
(2007/10/03)
-
- Solid phase synthesis of sulfonamides using a carbamate linker
-
A method for the synthesis of sulfonamides on a solid support by immobilizing amines through the nitrogen atom using a carbamate linkage is described.
- Raju,Kogan, Timothy P.
-
p. 3373 - 3376
(2007/10/03)
-
- Use of halomethyl resins to immobilize amines: An efficient method for synthesis of sulfonamides and amides on a solid support
-
Methods for the synthesis of chloromethyl and bromomethyl equivalents of Wang's resin are described. To explore the utility of this acid clearable resin, amines were immobilized through the nitrogen atom, further functionalized, and then cleaved under acid conditions.
- Raju,Kogan, Timothy P.
-
p. 4965 - 4968
(2007/10/03)
-