18271-17-5Relevant academic research and scientific papers
Synthesis, X-ray structural, characterization, NBO and HOMO-LUMO analysis using DFT study of 4-methyl-N-(naphthalene-1-yl)benzene sulfonamide
Sarojini, K.,Krishnan, H.,Kanakam, Charles C.,Muthu, S.
, p. 657 - 667,11 (2012)
The sulfonamide compound, 4-methyl-N-(naphthalene-1-yl)benzene sulfonamide (abbreviated as 4MNBS) was synthesized from the reaction of 4-methyl benzene sulfonyl chloride with 1-naphthyl amine. The 4MNBS was characterized by FTIR, 1H NMR, 1
One-scale basicities of diaminobenzenes and diaminonaphthalenes: from aniline to proton sponge
Vlasenko, Marina P.,Ozeryanskii, Valery A.
, (2017)
Basicity constants, pKa, for a wide range of mono-protonated diaminobenzenes and diaminonaphthalenes, including dimethylamino derivatives were for the first time uniformly measured in 20% aqueous ethanol (29 compounds) and 80% aqueous dioxane (39 compounds) spanning from aniline to 1,8-bis(dimethylamino)naphthalene (‘proton sponge’). The dioxane system proved to be more versatile and because of better solubility of N-alkylated polyaminoarenes allowed to add to the same scale some superbasic bis(dialkylamino)-, tetrakis(dialkylamino)-, and hexakis(dialkylamino)naphthalenes, thus extending the scale for almost 10 pKa units, revealing possible limits of basicity changes in aromatic amines. The basicity of reference bases, pyridine and triethylamine, was also measured in these solvent systems. A group of N-alkylated compounds was found to be less basic in aqueous dioxane when compared with their NH2-analogs. This anomaly was not observed in aqueous ethanol. Other basicity trends and correlations between different basicity scales were also discussed. Copyright
Sanguinarine as a new chemical entity of thioredoxin reductase inhibitor to elicit oxidative stress and promote tumor cell apoptosis
Yao, Juan,Duan, Dongzhu,Song, Zi-Long,Zhang, Junmin,Fang, Jianguo
, p. 659 - 667 (2020)
The alteration of redox homeostasis is a hallmark of cancer cells. As a critical player in regulating cellular redox signaling, thioredoxin reductase (TrxR) enzymes are increasingly recognized as attractive targets for anticancer drug development. We repo
Ruthenium-catalyzed cross-coupling of 7-azabenzonorbornadienes with alkynes. An entry to 3a,9b-dihydrobenzo[g]indoles
Tenaglia, Alphonse,Marc, Sylvain
, p. 1397 - 1402 (2008)
(Chemical Equation Presented) Electron-rich half-sandwich ruthenium complex CpRuI(PPh3)2, generated in situ, catalyzed the coupling reaction of 7-azabenzonorbornadienes with alkynes to form 3a,9b-dihydrobenzo[g] indoles. This transfo
A new generation of terminal copper nitrenes and their application in aromatic C-H amination reactions
Amarouch, Benedikt,G?bgen, Kai C.,Hoffmann, Alexander,Oster, Matthias,Sch?n, Florian,Steden, Dominik,Thomas, Fabian
supporting information, p. 6444 - 6462 (2021/05/26)
Copper nitrene complexes are highly reactive species and are known as intermediates in the copper catalyzed C-H amination. In this study, three novel copper tosyl nitrene complexes were synthesized at low temperatures, stabilized with heteroscorpionate ligands of the bis(pyrazolyl)methane family. The copper nitrenes were obtained by the reaction of a copper(i) acetonitrile complex with SPhINTs in dichloromethane. We show that the ligand design has a major influence on the catalytic activity and the thermal stability of the copper nitrene complex. Not only the choice of the third N donor, but also the substituent in the 5-position of the pyrazolyl moiety, have an impact on the stability. Furthermore, the novel copper nitrene complexes were used for catalytic aziridination of styrenes and C-H amination reactions of aromatic and aliphatic substrates under mild reaction conditions. Even challenging substrates like benzene and cyclohexane were aminated with good yields. The copper nitrene complexes were characterized using UV/Vis spectroscopy, low temperature Evans NMR spectroscopy, density functional theory, domain-based local pair natural orbital coupled cluster calculations (DLPNO-CCSD(T)) and cryo-UHR mass spectrometry.
Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides
Ferguson, Michael J.,McGuire, Ryan T.,Simon, Connor M.,Stradiotto, Mark,Yadav, Arun A.
supporting information, p. 8952 - 8956 (2020/05/01)
The development of Ni-catalyzed C?N cross-couplings of sulfonamides with (hetero)aryl chlorides is reported. These transformations, which were previously achievable only with Pd catalysis, are enabled by use of air-stable (L)NiCl(o-tol) pre-catalysts (L=P
Copper iodide nanoparticles-decorated porous polysulfonamide gel: As effective catalyst for decarboxylative synthesis of N-Arylsulfonamides
Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin,Rakhtshah, Jamshid,Yousefi Seyf, Jaber,Ali Arabian, Iman
, (2020/01/22)
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.
Lewis Base Promoted, Direct 1,4-Conjugate Addition to Quinone Imine Ketals: Efficient Access to Unsymmetrical Diaryl Sulfones
Liu, Teng,Liu, Jianjun,Shen, Xianfu,Xu, Jianbin,Nian, Beifang,He, Ni,Zeng, Shunqun,Cheng, Feixiang
, p. 1365 - 1376 (2019/03/08)
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.
Copper-catalyzed redox coupling of nitroarenes with sodium sulfinates
Liu, Saiwen,Chen, Ru,Zhang, Jin
, (2019/05/02)
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.
Au(i)/Au(iii)-Catalyzed C-N coupling
Rodriguez, Jessica,Adet, Nicolas,Saffon-Merceron, Nathalie,Bourissou, Didier
supporting information, p. 94 - 97 (2019/12/25)
Cycling between Au(i) and Au(iii) is challenging, so gold-catalyzed cross-couplings are rare. The (MeDalphos)AuCl complex, which we showed was prone to undergo oxidative addition, is reported here to efficiently catalyze the C-N coupling of aryl iodides and amines. The transformation does not require an external oxidant or a directing group. It is robust and works with a wide scope of aryl iodides and N-nucleophiles under mild conditions. Mechanistic studies, including the NMR and MS characterization of a key aryl amido Au(iii) complex, strongly support a 2e redox cycle in which oxidative addition precedes transmetalation and reductive elimination is the rate-determining step.
