766-94-9Relevant academic research and scientific papers
The phenyl vinyl ether–methanol complex: A model system for quantum chemistry benchmarking
Bernhard, Dominic,Dietrich, Fabian,Fatima, Mariyam,Pérez, Cristóbal,Gottschalk, Hannes C.,Wuttke, Axel,Mata, Ricardo A.,Suhm, Martin A.,Schnell, Melanie,Gerhards, Markus
, p. 1642 - 1654 (2018)
The structure of the isolated aggregate of phenyl vinyl ether and methanol is studied by combining a multi-spectroscopic approach and quantum-chemical calculations in order to investigate the delicate interplay of noncovalent interactions. The complementa
Enhanced bulk catalyst dissolution for self-healing materials
Mauldin, Timothy C.,Kessler, Michael R.
, p. 4198 - 4206 (2010)
A model was developed to aid in the selection of healing monomers that can rapidly dissolve catalysts in self-healing materials. Predictions are made regarding dissolution rates of Grubbs' catalyst in a small library of ring-opening metathesis polymerizat
Synthesis of vinyl phenyl ether and its use for ammetric titration of silver(I)
Nurmanov,Gevorgyan,Matmuratov,Kasimova,Sirlibaev,Kalyadin
, p. 480 - 482 (2002)
Catalytic vinylation of phenol with acetylene at atmospheric pressure was studied. The yield of vinyl phenyl ether was determined as influenced by the solvent, reaction temperature, and catalyst amount. The mechanism of formation of vinyl phenyl ether was proposed. Ammetric titration of silver(I) with a solution of vinyl phenyl ether in nonaqueous acetic acid solutions was performed.
Reductive C-O, C-N, and C-S Cleavage by a Zirconium Catalyzed Hydrometalation/β-Elimination Approach
Matt, Christof,K?lblin, Frederic,Streuff, Jan
supporting information, p. 6983 - 6988 (2019/09/09)
A zirconium catalyzed reductive cleavage of Csp3 and Csp2 carbon-heteroatom bonds is reported that makes use of a tethered alkene functionality as a traceless directing group. The reaction is successfully demonstrated on C-O, C-N, and C-S bonds and proposed to proceed via a hydrozirconation/β-heteroatom elimination sequence of an in situ formed zirconium hydride catalyst. The positional isomerization of the catalyst further enables the cleavage of homoallylic ethers and the removal of terminal allyl and propargyl groups.
Reusable rhodium catalyst for the selective transvinylation of sp2-C linked carboxylic acid
Jiang, Ruihang,Chen, Zhangpei,Zhan, Kun,Liu, Lei,Zhou, Junjie,Ai, Yongjian,Li, Shuang,Bao, Hongjie,Hu, Ze'nan,Qi, Li,Wang, Jingting,Sun, Hong-bin
, p. 3279 - 3282 (2018/07/21)
The vinyl benzoate derivatives were successfully synthesized by the transvinylation reactions that vinyl group transferred from vinyl acetate to aromatic carboxylic acids with the recoverable catalyst RhCl3·3H2O. This catalyst features air stable and tolerance of water, good reusable ability, meanwhile, shows high selectivity for aromatic carboxylic acid in the presence of phenolic hydroxyl. With this method, a variety of vinyl benzoate derivatives can be produced with up to 95% yield.
Vinylation of Aryl Ether (Lignin Β-O-4 Linkage) and Epoxides with Calcium Carbide through C?O Bond Cleavage
Teong, Siew Ping,Lim, Jenny,Zhang, Yugen
, p. 3198 - 3201 (2017/09/02)
Calcium carbide has been increasingly used as a sustainable, easy-to-handle, and low-cost feedstock in organic synthesis. Currently, methodologies of using calcium carbide as “solid acetylene” in synthesis are strictly limited to activation and reaction w
Direct vinylation of natural alcohols and derivatives with calcium carbide
Teong, Siew Ping,Chua, Ariel Yi Hui,Deng, Shiyun,Li, Xiukai,Zhang, Yugen
supporting information, p. 1659 - 1662 (2017/06/07)
Vinyl ethers are essential synthetic building blocks for organic synthesis, especially for polymer synthesis and highly vinylated polyol substrates. Herein, a transition metal-free, mild, and safe protocol has been developed for direct vinylation of natural alcohols with calcium carbide. Various sugar alcohols, phenol and its derivatives were tested and proved successful using this green methodology. Selectivity of full vinylated products of the reaction decreases with increasing hydroxyl groups because of side reactions occurring under the basic medium. Electron-donating substituted phenols work more efficiently than electron-withdrawing substituted phenols in general. This methodology may provide new insights on selective vinylation of electron-rich biomass-derived materials.
A solid acetylene reagent with enhanced reactivity: Fluoride-mediated functionalization of alcohols and phenols
Werner, Georg,Rodygin, Konstantin S.,Kostin, Anton A.,Gordeev, Evgeniy G.,Kashin, Alexey S.,Ananikov, Valentine P.
supporting information, p. 3032 - 3041 (2017/07/24)
The direct vinylation of an OH group in alcohols and phenols was carried out utilizing a novel CaC2/KF solid acetylene reagent in a simple K2CO3/KOH/DMSO system. The functionalization of a series of hydroxyl-group-containing substrates and the post-modification of biologically active molecules were successfully performed using standard laboratory equipment, providing straightforward access to the corresponding vinyl ethers. The overall process developed involves an atom-economical addition reaction employing only inorganic reagents, which significantly simplifies the reaction set-up and the isolation of products. A mechanistic study revealed a dual role of the F- additive, which both mediates the surface etching/renewal of the calcium carbide particles and activates the CC bond towards the addition reaction. The development of the fluoride-mediated nucleophilic addition of alcohols eliminates the need for strong bases and may substantially extend the areas of application of this attractive synthetic methodology due to increasing functional group tolerance. As a replacement for dangerous and difficult to handle high-pressure acetylene, we propose the solid reagent CaC2/KF, which is easy to handle, does not require dedicated laboratory equipment and demonstrates enhanced reactivity of the acetylenic triple bond. Theoretical calculations have shown that fluoride-mediated activation of the hydroxyl group towards nucleophilic addition significantly reduces the activation barrier and facilitates the reaction.
Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides
Nishimoto, Yoshihiro,Kita, Yuji,Ueda, Hiroki,Imaoka, Hiroto,Chiba, Kouji,Yasuda, Makoto,Baba, Akio
supporting information, p. 11837 - 11845 (2016/08/05)
A cross-coupling reaction between enol derivatives and silyl ketene acetals catalyzed by GaBr3took place to give the corresponding α-alkenyl esters. GaBr3showed the most effective catalytic ability, whereas other metal salts such as BF3?OEt2, AlCl3, PdCl2, and lanthanide triflates were not effective. Various types of enol ethers and vinyl carboxylates as enol derivatives are amenable to this coupling. The scope of the reaction with silyl ketene acetals was also broad. We successfully observed an alkylgallium intermediate by using NMR spectroscopy, suggesting a mechanism involving anti-carbogallation among GaBr3, an enol derivative, and a silyl ketene acetal, followed by syn-β-alkoxy elimination from the alkylgallium. Based on kinetic studies, the turnover-limiting step of the reaction using a vinyl ether and a vinyl carboxylate involved syn-β-alkoxy elimination and anti-carbogallation, respectively. Therefore, the leaving group had a significant effect on the progress of the reaction. Theoretical calculations analysis suggest that the moderate Lewis acidity of gallium would contribute to a flexible conformational change of the alkylgallium intermediate and to the cleavage of the carbon?oxygen bond in the β-alkoxy elimination process, which is the turnover-limiting step in the reaction between a vinyl ether and a silyl ketene acetal.
Heterogeneous Gold-Catalyzed Selective Semireduction of Alkynes using Formic Acid as Hydrogen Source
Li, Shu-Shuang,Tao, Lei,Wang, Fu-Ze-Rong,Liu, Yong-Mei,Cao, Yong
supporting information, p. 1410 - 1416 (2016/05/19)
A convenient and robust protocol for the selective transfer semireduction of alkynes was developed, using bio-renewable formic acid as the hydrogen source and easily handled supported gold nanoparticles as the catalyst. The catalytic system showed several attractive features such as high activity and selectivity, recyclability, scalability and adaptability to continuous operation under mild reaction conditions, thus providing a practical alternative to current methods for alkyne semireduction.
