1146-39-0Relevant academic research and scientific papers
Mechanistic aspects of copper (II)-catalyzed synthesis of sulfones from sulfinate salts and aryl halides under C-S coupling
Ge, Xin,Sun, Fengli,Liu, Xuemin,Chen, Xinzhi,Qian, Chao,Zhou, Shaodong
, p. 72 - 78 (2018)
Copper(II)-catalyzed synthesis of sulfones from sulfinate salts and aryl halides was investigated by means of a combination of experiment and DFT calculation. Experimental results demonstrated the wide applicability of the title approach. The reaction mechanisms are revealed by in-situ IR and theoretical study. It reveals remarkable ligand effect the bidentate amine plays in the reaction, that is, it initially activats the C-I bond of iodobenzene so as to enhance the whole catalytic process.
D-Glucosamine as a green ligand for copper catalyzed synthesis of aryl sulfones from aryl halides and sodium sulfinates
Yang, Ming,Shen, Hongyun,Li, Yuanyuan,Shen, Chao,Zhang, Pengfei
, p. 26295 - 26300 (2014)
d-Glucosamine is reported for the first time as a green ligand for copper catalyzed coupling of aryl halides and sodium sulfinates, which provides a simple and extremely efficient new route to unsymmetrical diaryl sulfones. The catalytic reaction proceeded in DMSO-H2O at 100°C and gave a variety of aryl sulfones in high yields. The high water solubility of the ligand enables easy catalyst removal. The scope of the method was validated by a single step synthesis of marketed drug zolimidine, a drug used for peptic ulcers, in 65% yield.
Synthesis and characterization of insoluble cobalt(II), nickel(II), zinc(II) and palladium(II) Schiff base complexes: Heterogeneous catalysts for oxidation of sulfides with hydrogen peroxide
Menati, Saeid,Amiri Rudbari, Hadi,Askari, Banafshe,Riahi Farsani, Mostafa,Jalilian, Fariba,Dini, Ghasem
, p. 347 - 356 (2016)
The condensation reaction of 1,2-bis(2'-aminophenoxy)benzene with 2-pyridinecarbaldehyde in a mole ratio of 1:2 gives a new Schiff base ligand (L). Four Schiff base complexes, CoL(NO3)2 (1), NiLCl2 (2), ZnL(NO3)2 (3) and Pd2LCl4 (4) have been prepared by direct reaction of the ligand (L) and appropriate metal salts. The Schiff base ligand (L) has been characterized by IR, 1H NMR and 13C NMR spectroscopy and elemental analysis. Also, all complexes have been characterized by IR and XRD spectroscopy techniques and elemental analysis. The synthesized complexes have very poor solubility in all polar and non-polar solvents such as: H2O, MeOH, EtOH, CH3CN, DMSO, DMF, CHCl3, CH2Cl2, THF, etc; therefore, they have been used as heterogeneous catalysts. Catalytic performance of the complexes was studied in oxidation of thioanisole using hydrogen peroxide (H2O2) as the oxidant. Various factors including the reaction temperature, amount of oxidant and catalyst amount were optimized. The palladium Schiff base complex, Pd2LCl4 (4), shows better catalytic activity than other complexes. Therefore, the Pd(II) Schiff base complex has been used as a catalyst for oxidation of different sulfides to their corresponding sulfones in acetonitrile with hydrogen peroxide as the oxidant. The palladium Schiff base complex, Pd2LCl4 (4), has shown a very good recyclability, up to five times, without any appreciable decreases in catalytic activity and selectivity.
Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water
Ge, Xin,He, Xi,Liu, Xuemin,Qian, Chao,Song, Weili,Yang, Jinguo,Zhou, Shaodong
, p. 6322 - 6329 (2021)
A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.
On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle
Ge, Xin,Lei, Qiuyun,Liao, Xiong,Liu, Xuemin,Song, Weili,Wu, Lei,Wu, Siyuan,Zhou, Shaodong
, (2021)
A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.
Effective Utilization of in Situ Generated Hydroperoxide by a Co-SiO2@Ti-Si Core-Shell Catalyst in the Oxidation Reactions
Liu, Meng,Shi, Song,Zhao, Li,Wang, Min,Zhu, Guozhi,Zheng, Xi,Gao, Jin,Xu, Jie
, p. 683 - 691 (2018)
A core-shell catalyst (Co-SiO2@Ti-Si) with cobalt-based SiO2 nanocomposite (Co-SiO2) as the core and Ti-doped mesoporous silica as the shell was designed to catalyze a one-pot reaction of sulfide oxidation with in situ generated hydroperoxide. The catalyst was characterized by SEM, TEM, UV-vis spectroscopy, and XPS, among other methods. Compared to Co-SiO2 and the physical mixture of the two components (Co-SiO2 + Ti-Si), the core-shell catalyst significantly enhanced the reaction rate of the sulfide oxidation. The utilization efficiency of the hydroperoxide was an important factor responsible for the differences in the reaction rates. A further mechanism study showed that the improvement of the efficiency was due to the existence of a coordination pathway. The core-shell structure of a bifunctional catalyst represents a strategy for improving the utilization efficiency of hydroperoxide.
A biradical oxo-molybdenum complex containing semiquinone and: o -aminophenol benzoxazole-based ligands
Galindo, Agustín,Jagli?i?, Zvonko,Masoumpour, Marzieh Sadat,Nasibipour, Mina,Safaei, Elham,Wojtczak, Andrzej
, p. 40853 - 40866 (2020)
We report a new mononuclear molybdenum(iv) complex, MoOLBISLSQ, in which LSQ (2,4-di-tert-butyl o-semibenzoquinone ligand) has been prepared from the reaction of the o-iminosemibenzoquinone form of a tridentate non-innocent benzoxazole ligand, LBIS, and MoO2(acac)2. The complex was characterized by X-ray crystallography, elemental analysis, IR and UV-vis spectroscopy and magnetic susceptibility measurements. The crystal structure of MoOLBISLSQ revealed a distorted octahedral geometry around the metal centre, surrounded by one O and two N atoms of LBIS and two O atoms of LSQ. The effective magnetic moment (μeff) of MoOLBISLSQ decreased from 2.36 to 0.2 μB in the temperature range of 290 to 2 K, indicating a singlet ground state caused by antiferromagnetic coupling between the metal and ligand centred unpaired electrons. Also, the latter led to the EPR silence of the complex. Cyclic voltammetry (CV) studies indicate both ligand and metal-centered redox processes. MoOLBISLSQ was applied as a catalyst for the oxidative cleavage of cyclohexene to adipic acid and selective oxidation of sulfides to sulfones with aqueous hydrogen peroxide. This journal is
Electrochemical investigation of the reaction between sodium benzenesulfinate and p-halonitrobenzenes
Balslev, Henrik,Lund, Henning
, p. 7889 - 7896 (1994)
Electrochemical evidence suggests that sodium benzenesulfinate reacts with the four p-halonitrobenzenes in a S(N)Ar-reaction, and not in a S(RN)2-reaction, as claimed by other authors.
A reconsideration of the mechanism for the aromatic version of radical nucleophile displacement reactions
Denney, Donald B.,Denney, Dorothy Z.
, p. 6577 - 6600 (1991)
A review of the literature and new experimental data indicate that aromatic radical anions containing leaving groups react with nucleophiles by a bimolecular displacement process.
Cu(I)-catalysed coupling of arylsulfinic salts with aryl bromides
Peng, Yao
, p. 447 - 449 (2014)
An efficient Cu(I)-catalysed synthesis of diaryl sulfones from arylsulfinic acid salts and aryl bromides in 1,3-dimethyl-2- imidazolidinone at 80 °C in the presence of CuBr and pyridine has been developed. The high-yielding process exhibits significant functional group tolerance and allows for the preparation of a number of diaryl sulfones under mild conditions.
