1655-74-9Relevant academic research and scientific papers
Electrochemical fluorination of aromatic compounds in anhydrous HF
Shainyan,Danilevich
, p. 214 - 219 (2006)
Electrochemical fluorination of anisole furnished 2- and 4-fluoroanisoles in a 3:1 ratio, guaiacol, and 4,4′-dimethoxydiphenyl ether. Phenylacetonitrile alongside the fluorination in the ring suffered the transformation of the cyano group into a trifluoromethyl. 4-Bromobenzamide was fluorinated to a high conversion mostly in the ring to afford predominantly 4-bromo-3,3,6,6-tetrafluoro-1,4-cyclohexadienecarboxamide. 4-Bromonitrobenzene in a low yield gave 4-bromofluoronitrobenzene and 3,4-dibromofluoronitrobenzene. 3-Bromo-nitrobenzene and 1,4-dichlorobenzene did not undergo fluorination. In the course of the electrolysis of the 4-bromobenzamide and 4-bromonitrobenzene in anhydrous HF apart the fluorination occurred also the bromination of the substrates. Pleiades Publishing, Inc. 2006.
Synthesis, experimental and theoretical investigation of molecular structure, IR, Raman spectra and 1H NMR analyses of 4,4′-dihydroxydiphenyl ether and 4,4′-oxybis(1-methoxybenzene)
Liu, Fu,Wei, Zhongbo,Wang, Liansheng,Wang, Zunyao
, p. 285 - 294 (2013)
4,4′-Dihydroxydiphenyl ether and 4,4′-oxybis(1-methoxybenzene) are synthesized. Experimental and theoretical studies on molecular structure, infrared spectra (IR), Raman spectra and nuclear magnetic resonance ( 1H NMR) chemical shifts of the two synthesized compounds have been worked out. All the theoretical results, which are obtained with B3LYP/6-311G(d,p) method by using the Gaussian 09 program, have been applied to simulate molecular structure, infrared, Raman and NMR spectra of the compounds. The compared results reveal that the calculated geometric parameters match well with experimental values; the scaled theoretical vibrational frequencies are in good accordance with observed spectra; and computational chemical shifts are consistent with the experimental values in most part, except for some minor deviations. These great coincidences prove that the computational method B3LYP/6-311G(d,p) can be used to predict the properties of other similar materials where it is difficult to arrive at experimental results.
Aromatic ether compound or the sulfhydryl compound
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Paragraph 0072; 0074; 0078; 0109, (2021/11/19)
[Problem] Aromatic ether compounds and aromatic sulfide compound of this new technology to[Solution] In general formula (1a), (1b), (1c) palladium or nickel compound or a phosphine compound represented by the compound comprising a transition metal compound in the presence of a transition metal catalyst, (A1) is represented by compounds having hydroxy carbon C a-OH or (A2) with a compound represented by the sulfhydryl carbon C a-SH, nitro group (- NO2 ) To react with an aromatic nitro compound (B), (A1) to the compound of the aromatic nitro compound (C1) or the reaction product of an aromatic ether compounds (B) hetero coupling (A2) of the compounds of the reaction product of an aromatic sulfide compound of an aromatic nitro compound (C2) generating (B) hetero coupling characterized by comprising the step of, aromatic ether compounds or aromatic sulfide compound. [Drawing] no
Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers
Ray, Ritwika,Hartwig, John F.
supporting information, p. 8203 - 8211 (2021/03/08)
Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0134-0139, (2021/05/29)
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
A novel magnetic polyacrylonotrile-based palladium Core?Shell complex: A highly efficientcatalyst for Synthesis of Diaryl ethers
Eslami, Mohammad,Jarahiyan, Atefeh,Moghaddam, Firouz Matloubi,Pourjavadi, Ali
, (2020/04/15)
The present article describes the synthesis of a new magnetic polyacrylonitrile-based Pd catalyst involving polyacrylonitrile modified via 2-aminopyridine as an efficient support to immobilize Pd nanoparticles. The simple reusability, easy separation and high stability of this Pd complex make it an excellent candidate to generate a C–O bond via Ph-X activation which is a really important subject in achieving biologically active compounds. It is worth to note access to good and high yields as well as broad substrate scope have resulted from superior reactivity of this catalyst complex. Furthermore, the structure of the magnetic polyacrylonitrile-based heterogeneous catalyst was characterized by fourier transmission infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM), X-ray diffraction (XRD). Also, its thermal properties were studied by thermogravimetric analysis (TGA).
Identification of an Oxalamide Ligand for Copper-Catalyzed C?O Couplings from a Pharmaceutical Compound Library
Chan, Vincent S.,Krabbe, Scott W.,Li, Changfeng,Sun, Lijie,Liu, Yue,Nett, Alex J.
, (2019/04/30)
A typical pharmaceutical compound library is stocked with molecular diversity and could provide a platform for the discovery of new ligand structures. Herein, we describe the use of this approach in combination with high throughput screening to identify N,N’-bis(thiophene-2-ylmethyl)oxalamide as a ligand that is generally effective for copper-catalyzed C?O cross-couplings to prepare both biarylethers as well as phenols under mild conditions.
The First C?Cl Activation in Ullmann C?O Coupling by MOFs
Ramezani, Leila,Yahyazadeh, Asieh,Sheykhan, Mehdi
, p. 4636 - 4651 (2018/09/21)
It was found that introduction of only 0.03 mol % Ag(I) into the framework of Cu3(BTC)2 ? xH2O in maghemite anchored CuBTC activated the inert CuBTC astonishingly to exhibit unexpected high catalytic activity for C?Cl activation in coupling of chloroarenes with phenols without the use of expensive ligands. This is the first application of mixed-metal MOFs in the C?X activation. Putting reusability and activity together, a TON over 15000 was obtained which is the highest TON compared with all its precedents even better than the results by Pd catalysts.
Palladium-Catalyzed Formal Cross-Coupling of Diaryl Ethers with Amines: Slicing the 4-O-5 Linkage in Lignin Models
Zeng, Huiying,Cao, Dawei,Qiu, Zihang,Li, Chao-Jun
supporting information, p. 3752 - 3757 (2018/03/13)
Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C?C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)?O bond cleavages form valuable nitrogen-containing derivatives.
Immobilized palladium nanoparticles on MNPs@A-N-AEB as an efficient catalyst for C-O bond formation in water as a green Solvent
Moghaddam, Firouz Matloubi,Eslami, Mohammad
, (2018/08/24)
Palladium nanoparticles immobilized on the magnetic nanoparticles@2-amino-N-(2-aminoethyl) benzamide (MNPs@A-N-AEB.Pd0) have been presented as an efficient, and reusable magnetically heterogeneous catalyst for the C-O coupling reaction, namely Ullmann condensation reactions in an aqueous medium. This heterogeneous catalyst shows superior reactivity for the C-O arylation of different aryl halide (chloride, bromide, and iodide) with phenol derivatives to afford the desired products in good to excellent yields within short reaction time. Moreover, the catalyst can be easily recovered and reused for seven runs without loss of catalytic activity. The catalyst was characterized by several techniques, such as FT-IR, SEM, TEM, EDS, XRD, TGA and ICP-OES.
