101-63-3Relevant articles and documents
Microwave-assisted construction of diaryl ethers directly from arylmethanesulfonates as convenient latent phenols with aryl halides
Xu, Hui,Chen, Yang
, p. 2411 - 2420 (2007)
The microwave-assisted synthesis of diaryl ethers directly from aryl halides and arylmethanesulfonates, which as latent phenols obviate a deprotection step prior to the SNAr reaction, in the presence of Cs2CO3 is described. The reaction time was very short (6-9-min), and good to excellent yields (53-90%) with the wide substrate scope were achieved without any catalyst. Copyright Taylor & Francis Group, LLC.
A new strategy to design a graphene oxide supported palladium complex as a new heterogeneous nanocatalyst and application in carbon–carbon and carbon-heteroatom cross-coupling reactions
Bahrami, Kiumars,Targhan, Homa
, (2019)
The palladium nanoparticles were successfully stabilized with an average diameter of 6–7?nm through the coordination of palladium and terpyridine-based ligands grafted on graphene oxide surface. The graphene oxide supported palladium nanoparticles were thoroughly characterized and applied as an efficient heterogeneous catalyst in carbon–carbon (Suzuki-Miyaura, Mizoroki-Heck coupling reactions) and carbon–heteroatom (C-N and C-O) bond-forming reactions. The catalyst was simply recycled from the reaction mixture and was reused consecutive four times with small drop in catalytic activity.
Eyring Activation Barriers for the Anomalous Dielectric Relaxations of Diphenyl Ether Type Molecules
Chao, J.,Desando, M. A.,Gourlay, D. L.,Orr, D. E.,Walker, S.
, p. 711 - 716 (1984)
Several symmetrically substituted diaryl ethers have been studied in a polystyrene matrix and bis(4-nitrophenyl) ether also in glassy o-terphenyl by dielectric adsorption techniques in the frequency range 10-1E5 Hz over temperatures of 77-323 K.Bis(4-cyanophenyl) ether in polystyrene was also examined at many temperatures in the frequency range E-4-E-7Hz.In the polystyrene matrix both the molecular and intramolecular relaxation processes were detected for diphenyl ether and bis(4-nitrophenyl) ether.An intramolecular relaxation process was detected for most of the aromatic ethers, and the associated Eyring enthalpy of activation is ca. 10 kJ mol-1.Which is similar to that observed for some alkyl aryl ethers in the same media.The present work establishes that the energy barrier for rotation around the C-O bonds is symmetrically substituted diphenyl ethers is very low and that intramolecular motion would be expected to occur quite readily about these bonds.
Design of BNPs-TAPC Palladium Complex as a Reusable Heterogeneous Nanocatalyst for the O-Arylation of Phenols and N-Arylation of Amines
Bahrami, Kiumars,Khodamorady, Minoo
, p. 688 - 698 (2019)
The thermally stable new heterogenous nanocatalyst BNPs@SiO2(CH2)3-TAPC-O-CH2CH2NH2-Pd(0) was synthesized, characterized and successfully applied in carbon-heteroatom (C–O and C–N) coupling reactions of aryl halides with phenols and amines. The formation of resultant nanocatalyst was approved by FT-IR, XRD, TGA, XPS and EDX techniques. The morphology of BNPs@SiO2(CH2)3-TAPC-O-CH2CH2NH2-Pd(0) was characterized using scanning and transmission electron microscopes. The leaching of palladium from the surface of the catalyst was studid by ICP-OES technique. Noteworthy, the highly active BNPs@SiO2(CH2)3-TAPC-O-CH2CH2NH2-Pd(0) can be easily recycled and reused for six times with negligible loss in its activity. Some remarkable advantages of this method are the shorter reaction times, milder conditions, no needs for an inert atmosphere, high yields and easy separation. Graphical Abstract: [Figure not available: see fulltext.].
A PEG1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system that regulates homogeneously catalyzed C-O coupling of organic halides with phenols and alcohols under ligand-free conditions
Hu, Yu Lin,Ma, Xiao Yun,Lu, Ming
, p. 471 - 480 (2011)
An efficient, experimentally simple, and convenient procedure for the C-O coupling of organic halides with phenols and alcohols in a PEG 1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
Synthesis of symmetrical diaryl ethers from arylboronic acids mediated by copper(II) acetate
Sagar,Tale,Adude
, p. 7061 - 7063 (2003)
Copper promoted generation of phenols in situ through arylation of water and their subsequent arylation with arylboronic acids affords a wide range of symmetrical diaryl ethers in good to high yield. The reaction is rapid, mild, convenient and tolerant of a wide range of functionalities on the arylboronic acid.
Study of ultrasound promoted aromatic nucleophilic substitution of halobenzenes with amines
Meciarova, Maria,Toma, Stefan,Podlesna, Jana,Kiripolsky, Michal,Cisarova, Ivana
, p. 37 - 43 (2003)
The sonochemical nucleophilic aromatic substitution of substituted haloarenes with different amines were studied. The reaction course was found to be strongly depended on basicity, bulkiness, and boiling point of amines as well as on the electron-withdrawing property of the substituents.
Ultrasound synthesis of diaryl ethers
Begunov,Valyaeva,Belyaev,Dobretsova
, p. 1971 - 1974 (2015)
2,2-Bis[4-(4-nitroaryl)phenyl]hexafluoropropanes appropriate for the synthesis of monomers were prepared by the reaction of 2,2-bis[4-hydroxyphenyl)hexafluoropropane with 1-chloro-4-nitrobenzenes under ultrasonic activation.
C(aryl)-O bond formation from aryl methanesulfonates via consecutive deprotection and SNAr reactions with aryl halides in an ionic liquid
Xu, Hui,Chen, Yang
, p. 861 - 867 (2007)
An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methanesulfonates and a nucleophilic aromatic substitution (SNAr) with activated aryl halides.
Synthesis of diaryl ethers, diaryl sulfides, heteroaryl ethers and heteroaryl sulfides under microwave dielectric heating
Li, Feng,Meng, Qingqing,Chen, Huansheng,Li, Zhiming,Wang, Quanrui,Tao, Fenggang
, p. 1305 - 1313 (2005)
This paper describes the synthesis of diaryl ethers and sulfides by utilizing microwave heating methodology. The methodology is shown to be rapid and efficient for the coupling of phenols or thiophenol with electron-deficient aryl halides through a SNAr reaction. The scope of the protocol can be expanded to six-membered heterocycles bearing a hydroxyl group as well as to the reaction of 2-pyrimidinethiol with mildly activated aryl halides, providing heteroaryl ethers and sulfides, respectively. The advantages of the present method include the wide substrate scope, the obviation of metal catalysts, ease of product isolation, and high purity of products. Georg Thieme Verlag Stuttgart.
