1146-39-0Relevant articles and documents
Novel Synthesis of 4-benzaldehydes: Alkyl(aryl)sulfinate Anion as a Nucleophile in Aromatic Substitutions
Ulman, Abraham,Urankar, Edward
, p. 4691 - 4692 (1989)
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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.
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.
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
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.
A highly active and easily recoverable chitosan@copper catalyst for the C-S coupling and its application in the synthesis of zolimidine
Shen, Chao,Xu, Jun,Yu, Wenbo,Zhang, Pengfei
, p. 3007 - 3012 (2014)
Aryl sulfones were synthesized using a highly active and easily recoverable heterogeneous Cu catalyst which was prepared by simply stirring an aqueous suspension of chitosan in water with copper salts. The chitosan@copper catalyst catalyzed the coupling reactions of aryl halides with sodium sulfinates to readily give the corresponding sulfones in good to excellent yields. The highly active catalyst can be reused many times without losing its catalytic activity. In addition, by using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily. This journal is the Partner Organisations 2014.
Solvent free oxidation of sulfides to sulfones by H2O2 in the presence of chromium substituted polyoxometalate as catalyst
Afrasiabi, Roozbeh,Jalilian, Fariba,Yadollahi, Bahram,Farsani, Mostafa Riahi
, p. 113 - 116 (2014)
Solvent-free oxidation of sulfides into sulfones by 30% hydrogen peroxide has been achieved using chromium substituted Keggin type polyoxometalate under mild reaction conditions in 94-100% yield. This catalytic system showed excellent activity in the oxidation of sulfide groups. The other active functional groups such as hydroxyl and C=C bond have been tolerated.
Mo(VI) complex catalysed synthesis of sulfonees and their modification for anti-HIV activities
Madduluri, Vimal Kumar,Baig, Noorullah,Chander, Subhash,Murugesan, Sankaranarayanan,Sah, Ajay K.
, (2020/01/23)
An efficient method for the synthesis of sulfones has been developed using sugar derived cis-dioxo molybdenum(VI) complex as catalyst and urea hydrogen peroxide as oxygen source. Present method is highly specific for sulfide oxidation irrespective of presence of alkene and aldehyde groups in the same molecule. Synthesis of fifteen sulfones have been reported with 82–98% isolated yields and the catalyst has been reused five times without any loss in its activity. 2-(Phenylsulfonyl)aniline has been condensed with eight different aromatic aldehydes and the products are being explored for HIV-1 reverse transcriptase inhibition activities.