21668-99-5Relevant academic research and scientific papers
Synthesis, spectral characterization, SC-XRD, HSA, DFT and catalytic activity of novel dioxovanadium(V) complex with aminobenzohydrazone Schiff base ligand: An experimental and theoretical approach
Ashfaq, Muhammad,Behjatmanesh-Ardakani, Reza,Fallah-Mehrjardi, Mehdi,Kargar, Hadi,Munawar, Khurram Shahzad,Tahir, Muhammad Nawaz
, (2021/07/28)
A new dioxovanadium(V) complex was prepared by the reaction of VO(acac)2 with a tridentate ONO donor Schiff base, derived by condensing 3-ethoxysalicylaldehyde and 4-aminobenzohydrazide. The structures of synthesized products were characterized spectroscopically through FT-IR, 1H & 13C NMR and by elemental composition through combustion analysis. The structure of the complex was determined with the help of single crystal X-ray crystallography. It was inferred from the diffraction data that the geometry around the central metal ion in the complex is distorted square pyramidal. The tridentate Schiff base ligand is bonded to the central metal through the oxygen of the carbonyl group, the deprotonated phenolic oxygen atom and the azomethine nitrogen. The pyramid base is completed by other oxo ligands that are in cis positions. The theoretical calculations, performed by DFT using B3LYP/Def2-TZVP level of theory, determined that the intended outcomes are in compliance with the actual consequences. Furthermore, the catalytic potential of the vanadium complex was explored for the selective oxidation of the aryl and alkyl sulfides to the corresponding sulfones in the presence of 30% aqueous H2O2 in ethanol. In this work, rPBE and B3LYP methods are used to locate transition structures and to compare free energies of reactants, transition structures and the products involved in the reaction. Analyzing nudge elastic band data shows that the barrier free energy for the oxidation of sulfide to sulfoxide and sulfone are 13 and 83 kcal.mol?1, respectively. The main advantages of the present catalytic study are high yields of the products, less time required for the completion of the reaction and simple work-out procedure.
Vanadium-catalyzed Selective Oxidation of Sulfides to Sulfoxides and Sulfones with H2O2
Chen, M.,Jia, A.-Q.,Zhang, P.-Z.,Zhang, Q.-F.,Zhou, W.-Y.
, p. 816 - 824 (2021/06/12)
Abstract: A direct selective approach to the oxidation of sulfides to sulfoxides andsulfones with H2O2 in moderate togood yields is developed. The reaction proceeds in the presence of 2 mol % ofVO(acac)2 at room temperature. All sulfoxides andsulfones were detected by gas chromatography, and the molecular structures of2-methylbenzyl 4-methylphenyl sulfone, 4-methylbenzyl 4-methylphenyl sulfone,2-bromobenzyl 4-methylphenyl sulfone, and 4-tert-butylbenzyl benzyl sulfone were determined by singlecrystal X-ray crystallography.
Synthesis, spectra (FT-IR, NMR) investigations, DFT, FMO, MEP, NBO analysis and catalytic activity of MoO2(VI) complex with ONO tridentate hydrazone Schiff base ligand
Behjatmanesh-Ardakani, Reza,Fallah-Mehrjardi, Mehdi,Kargar, Hadi,Munawar, Khurram Shahzad
, (2021/08/16)
A new dioxomolybdenum(VI) complex has been successfully prepared by the reaction of an ONO donor Schiff base, derived by condensing 4-amino-2-hydroxybenzohydrazide and 3-ethoxysalicylaldehyde, with MoO2(acac)2. The structures of synthesized products were explored spectroscopically through FT-IR, 1H & 13C NMR and by elemental composition (CHN) through combustion analysis. The tridentate Schiff base ligand is bonded to the central metal through its deprotonated enolic and phenolic oxygen atoms and by the nitrogen of the azomethine group. The interpretation of the data obtained through diffraction analysis validates the distorted octahedral geometry for the prepared metal complex. Furthermore, the catalytic potential of the molybdenum complex was explored for the selective oxidation of the aryl and alkyl sulfides to the corresponding sulfones in the presence of 30% aqueous H2O2 in ethanol. The main edge of the present catalytic work is the accomplishment of reaction in a short period of time, high percentage yield and easy work-up procedure.
Synthesis of sulfone derivatives via palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides
Luo, Jin,Wan, Juelin,Wang, Tao,Yu, Weijie
supporting information, (2021/12/31)
A palladium-catalyzed cross-coupling of benzyl trimethylammonium triflates and sulfonyl hydrazides for the synthesis of various benzyl sulfones is reported. This novel protocol shows widespread functional group tolerance, leading to the desired sulfones in moderate to excellent yields.
Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones
Huang, Xiang,Chen, Xing,Xie, Haisheng,Tan, Zheng,Jiang, Huanfeng,Zeng, Wei
, p. 6784 - 6788 (2021/09/08)
A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
, p. 1377 - 1384 (2021/06/06)
We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.
Curbed of molybdenum oxido-diperoxido complex on ionic liquid body of mesoporous Bipy-PMO-IL as a promising catalyst for selective sulfide oxidation
Ahadi, Arefeh,Dugheri, Stefano,Hasanzadeh, Amir,Kavetskyy, Taras,Khaksar, Samad,Mamba, Bhekie B.,Moaser, Azra Ghiasi,Msagati, Titus A.-M.,Rostamnia, Sadegh,Rouhani, Shamila,Shokouhimehr, Mohammadreza
, (2020/06/08)
In this work, we introduce a novel bipyridinium ionic liquid bridged periodic mesoporous organosilicas (Bipy-PMOs-IL) which is used as the support to immobilize oxygen-rich Molybdenum (VI)-based oxido-peroxido complex (MoO(O2)2?Bipy-PMO-IL). Several techniques such as Small-angle X-ray scattering (SAXS), low angle XRD, FE-SEM (field emission scanning electron microscope), TEM (transmission electron microscope), N2 adsorption-desorption analyses (BET), atomic absorption spectroscopy (AAS), Fourier-transform infrared spectroscopy (FT-IR) and Energy Dispersive X-Ray (EDS or EDX) were used to characterize this nanomaterial. Also, the catalytic activities of the MoO(O2)2?Bipy-PMO-IL as a hybrid catalyst is tested in the selective oxidation of sulfides in water by using H2O2 (30%) as an eco-friendly and green co-oxidant. The as-prepared novel catalyst shows high to excellent performance under optimum reaction conditions at ambient room temperature. The obtained results in this work show several outstanding advantages, such as green conditions, high product yields, easy work-up, easy preparation and acceptable reusability of the catalyst for at least 5 runs. To study the IL effect in immobilization of Mo-complex, in a comparison study, the MoO(O2)2?Bipy-PMO-IL materials and MoO(O2)2?SBA-15 (with simple SiO2 body, no IL) body were employed for sulfide oxidation. After the treatment, the Mo?Bipy-PMO-IL with IL body in channels was reused for subsequent experiments (5 runs), but in Mo?SBA-15 after second run the yield was decreased dramatically.
A general and practical sulfonylation of benzylic ammonium salts with sulfonyl hydrazides for the synthesis of sulfones
Zhu, Haibo,Zhang, Yingying,Liu, Yishuai,Yang, Liu,Xie, Zongbo,Jiang, Guofang,Le, Zhang-Gao
, (2020/05/06)
A practical and efficient approach adopting transition-metal-free cross-coupling of sulfonyl hydrazides with benzyl ammonium salts has been developed to synthesize benzyl sulfones using Cs2CO3 as base under mild conditions. The protocol employs stable and easy to handle coupling partners, and is endowed with good substrate compatibility, leading to functional benzyl sulfones in good yields.
Reusable BNPs-SiO2@(CH2)3NHSO3H-catalysed selective oxidation of sulfides to sulfones
Bahrami, Kiumars,Khodamorady, Minoo
, (2018/10/15)
Reusable boehmite nanoparticles–silica–NHSO3H (BNPs-SiO2@(CH2)3NHSO3H) was found to be an efficient heterogeneous nanocatalyst for the selective oxidation of sulfides to sulfones in the presence of H2O2. Excellent yields, easy and quick isolation of products, short reaction times and excellent selectivity are the main advantages of this method. The catalyst was characterized using Fourier transform infrared spectroscopy, energy-dispersive X-ray analysis, X-ray diffraction, and transmission and scanning electron microscopies.
Palladium Catalyzed Monoselective α-Arylation of Sulfones and Sulfonamides with 2,2,6,6-Tetramethylpiperidine·ZnCl·LiCl Base and Aryl Bromides
Knauber, Thomas,Tucker, Joseph
, p. 5636 - 5648 (2016/07/14)
A palladium catalyzed Negishi-type α-arylation of sulfones and sulfonamides with a broad range of aryl bromides has been developed. The substrates are selectively metalated in situ with tmp·ZnCl·LiCl base (tmp: 2,2,6,6-tetramethylpiperidine) and cross-coupled in the presence of a catalyst system that is generated from Pd(dba)2 and XPhos. Electron-deficient, electron-rich, and heterocyclic aryl bromides have been successfully cross-coupled, and sensitive functional groups are well tolerated. Simple aryl bromides are converted overnight at 60 °C in THF while heteroaryl bromides are efficiently coupled within 2 h at 130 °C in a microwave reactor. The desired monoarylated α-branched benzyl sulfones and sulfonamides were obtained in good yields, and overarylation was not detected. The procedure is ideal for late stage functionalization in parallel medicinal chemistry.
