2715-43-7Relevant articles and documents
Synthesis, structure and characterization of two solvatochromic metal-organic frameworks for chemical-sensing applications
Gao, Sheng,Zhao, Limin,Han, Lin,Zhang, Zhenjie,Zhao, Hong
, p. 2237 - 2240 (2018)
Two isostructural Zr and Hf metal-organic frameworks (PU-1 and PU-2) were constructed from a hitherto unreported anthracene-derived dicarboxylate ligand and inorganic [M6O4(OH)4(CO2)12] (M = Zr4+ or Hf4+) secondary building unit under solvothermal conditions. They crystallized in the cubic Fd3m space group with doubly interpenetrated fcu-c topology. PU-1 exhibited an eye-catching color change within different solvents (especially in water) and could be a solvatochromic sensing material for recognition of solvent molecules.
Highly selective electroreductive linear dimerization of electron-deficient vinylarenes
Ning, Shulin,Zheng, Lianyou,Bai, Ya,Wang, Shutao,Wang, Siyu,Shi, Lingling,Gao, Qiansong,Che, Xin,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, (2021/11/16)
A direct electroreductive dimerization of electron-deficient vinylarenes for the synthesis of 1,4-diarylbutane has been developed using a simple undivided cell with inexpensive carbon electrodes at room temperature. The control and deuterium-labeling experiments of electroreductive dimerization suggest that the hydrogen source comes from the solvent CH3CN. This protocol provides a mild and efficient route for the construction of C–C bond in moderate to good yields with high regioselectivity and broad substrate scope.
Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications
Engl, Sebastian,Reiser, Oliver
supporting information, p. 5581 - 5586 (2021/07/26)
Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.
Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane
Wei, Shichao,Mao, Yongjun,Shi, Shi-Liang
supporting information, p. 1670 - 1674 (2021/02/26)
We herein disclose the first Ni-catalyzed Hiyama coupling of aryl halides with vinylsilanes. This protocol uses cheap, nontoxic, and stable vinyltrimethoxysilane as the vinyl donor, proceeds under mild and ligand-free conditions, furnishing a diverse variety of styrene derivatives in high yields with excellent functional group compatibility.
Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone
Valentini, Federica,Ferlin, Francesco,Lilli, Simone,Marrocchi, Assunta,Ping, Liu,Gu, Yanlong,Vaccaro, Luigi
supporting information, p. 5887 - 5895 (2021/08/23)
Herein we report a simple protocol for the valorisation of a common urban biowaste. The lignocellulosic biomass obtained after the pre-treatment of pine needle urban waste is efficiently transformed into a low-cost support (PiNe) for the immobilization of Pd nanoparticles. The final Pd/PiNe heterogeneous catalyst features a small particle size (4.5 nm) and a metal loading (9.9 wt%) comparable with most commercially available and generally used counterparts. In this contribution, we tested the catalytic efficiency of the Pd/PiNe system in two representative cross-couplings, Heck and Hiyama reactions, and compared the results obtained with commercial Pd/C catalyst. The good reactivity in the biomass-derived solvent (GVL) confirms that the Pd/PiNe heterogeneous catalyst is a valid system that can be integrated into a waste valorization chain within a circular economy approach. In addition, the efficiency of the catalyst has also been extended to perform the challenging consecutive Hiyama-Heck reaction to afford differently substituted (E)-1,2-diarylethenes.
Carbosulfenylation of Alkenes with Organozinc Reagents and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate
Tang, Meizhong,Han, Shuxiong,Huang, Shenglan,Huang, Shenlin,Xie, Lan-Gui
supporting information, p. 9729 - 9734 (2020/12/21)
The electrophilic alkylthiolation of alkenes, initiated by dimethyl(methylthio)sulfonium salts and the subsequent addition of various heteronucleophilies has been well-established. Regarding the use of carbon nucleophiles, however, only carefully designed sp-type carbon sources have been successfully applied. We herein present our findings on the methylthiolation of alkenes with dimethyl(methylthio)sulfonium trifluoromethanesulfonate, followed by carbon-carbon bond formation in the presence of organozinc reagents, thus achieving a catalyst-free protocol toward to the carbosulfenylation of alkenes.
Palladium-Catalyzed Three-Component Coupling of Ynamides
Wakamatsu, Hideaki,Takahashi, Ayano,Ishii, Ayaka,Kikuchi, Youhei,Sasaki, Madoka,Saito, Yukako,Natori, Yoshihiro,Yoshimura, Yuichi
supporting information, p. 5299 - 5303 (2020/07/08)
A palladium-catalyzed regioselective three-component coupling of ynamides was developed. The reaction proceeded smoothly to furnish the desired products when carried out at 70 °C in acetonitrile/water with potassium carbonate in the presence of 2.5 mol percent Pd2(dba)3·CHCl3 without a ligand. Various iodides and boronic acids were used in this reaction, and a carbon-carbon bond was formed with satisfactory regioselectivity from the ynamides.
Construction of Esters through Sulfuryl Fluoride (SO 2 F 2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature
Qin, Hua-Li,S Alharbi, Njud,Wang, Shi-Meng
, p. 3901 - 3907 (2019/10/11)
A facile method for the construction of esters through dehydrative coupling of carboxylic acids with alcohols is developed. The reactions are mediated by sulfuryl fluoride (SO 2 F 2) at room temperature and proceed with high efficiency. The method has several advantages including broad substrate scope, mild conditions, excellent functional group compatibility and affords high yields, even on gram scale.
Pd-Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid
Gao, Yang,Ou, Yang,Goo?en, Lukas J.
supporting information, p. 8709 - 8712 (2019/06/17)
Acrylic acid is presented as an inexpensive, non-volatile vinylating agent in a palladium-catalyzed decarboxylative vinylation of aryl halides. The reaction proceeds through a Heck reaction of acrylic acid, immediately followed by protodecarboxylation of the cinnamic acid intermediate. The use of the carboxylate group as a deciduous directing group ensures high selectivity for monoarylated products. The vinylation process is generally applicable to diversely substituted substrates. Its utility is shown by the synthesis of drug-like molecules and the gram-scale preparation of key intermediates in drug synthesis.
Evaluation of Potential Safety Hazards Associated with the Suzuki-Miyaura Cross-Coupling of Aryl Bromides with Vinylboron Species
Yang, Qiang,Canturk, Belgin,Gray, Kaitlyn,McCusker, Elizabeth,Sheng, Min,Li, Fangzheng
, p. 351 - 359 (2018/03/22)
The potential safety hazards associated with the Suzuki-Miyaura cross-coupling of aryl bromides with vinylboron species were evaluated. In the Suzuki-Miyaura cross-coupling of 1-bromo-3-(trifluoromethyl)benzene with potassium vinyltrifluoroborate in the presence of potassium carbonate (K2CO3) in 9:1 dimethyl sulfoxide (DMSO)/water at 80 °C, the thermal profile revealed a significant exotherm upon the addition of catalytic 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride [Pd(dppf)Cl2]. Further investigations indicated that the exotherm was consistently higher and the reactions were faster in the studied aqueous systems compared to anhydrous conditions. Although under anhydrous conditions the exotherms were comparable among the studied cases, the rate of the exotherm was highly dependent on the choice of aryl electrophile, solvent, base, catalyst, as well as vinylboron species. In many of the studied cases the maximum temperature of a synthesis reaction (MTSR) was considerably higher than the boiling point of the solvent and/or the onset temperature of the DMSO decomposition, indicating that in the absence of active cooling the system could quickly exceed the boiling point of the solvent or trigger the decomposition of the reaction mixture to result in a runaway reaction.
