- Ligand- and Counterion-Assisted Phenol O-Arylation with TMP-Iodonium(III) Acetates
-
High reactivity of trimethoxyphenyl (TMP)-iodonium(III) acetate for phenol O-arylation was achieved. It was first determined that the TMP ligand and acetate anion cooperatively enhance the electrophilic reactivity toward phenol oxygen atoms. The proposed method provides access to various diaryl ethers in significantly higher yields than the previously reported techniques. Various functional groups, including aliphatic alcohol, boronic ester, and sterically hindered groups, were tolerated during O-arylation, verifying the applicability of this ligand- and counterion-assisted strategy.
- Kikushima, Kotaro,Miyamoto, Naoki,Watanabe, Kazuma,Koseki, Daichi,Kita, Yasuyuki,Dohi, Toshifumi
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p. 1924 - 1928
(2022/03/27)
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- Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes
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A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.
- Yu, Congjun,?zkaya, Bünyamin,Patureau, Frederic W.
-
supporting information
p. 3682 - 3687
(2021/02/01)
-
- Nickel-Catalyzed Etherification of Phenols and Aryl Halides through Visible-Light-Induced Energy Transfer
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Notwithstanding some progress in nickel-catalyzed etherification of alkanols and arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one as the photosensitizer under visible light. This photocoupling exhibits a broad substrate scope.
- Zhu, Da-Liang,Jiang, Shan,Wu, Qi,Wang, Hao,Li, Hai-Yan,Li, Hong-Xi
-
supporting information
p. 8327 - 8332
(2021/10/25)
-
- Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers
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Herein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way, aryl iodides are used as reagents in a metal-free reaction with phenols, and a trimethoxyphenyl (TMP) group is used as a “dummy” group to facilitate transfer of a wide range of aryl moieties. The scope of aryl electrophiles and phenol nucleophiles is broad (>30 examples) and the yields are high (52–95%, 80% avg.). One-pot coupling reactions avoid the synthesis of diaryliodonium salts and provide opportunities for sequential reactions and novel chemoselectivity. (Figure presented.).
- Gallagher, Rory T.,Basu, Souradeep,Stuart, David R.
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p. 320 - 325
(2019/12/11)
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- In vitro antimycobacterial activity and physicochemical characterization of diaryl ether triclosan analogues as potential inhA reductase inhibitors
-
Two sets of diphenyl ether derivatives incorporating five-membered 1,3,4-oxadiazoles, and their open-chain aryl hydrazone analogs were synthesized in good yields. Most of the synthesized compounds showed promising in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Three diphenyl ether derivatives, namely hydrazide 3, oxadiazole 4 and naphthylarylidene 8g exhibited pronounced activity with minimum inhibitory concentrations (MICs) of 0.61, 0.86 and 0.99 μg/mL, respectively compared to triclosan (10 μg/mL) and isoniazid (INH) (0.2 μg/mL). Compounds 3, 4, and 8g showed the InhA reductase enzyme inhibition with higher IC50 values (3.28-4.23 μM) in comparison to triclosan (1.10 μM). Correlation between calculated physicochemical parameters and biological activity has been discussed which justifies a strong correlation with respect to the inhibition of InhA reductase enzyme. Molecular modeling and drug-likeness studies showed good agreement with the obtained biological evaluation. The structural and experimental information concerning these three InhA inhibitors will likely contribute to the lead optimization of new antibiotics for M. tuberculosis.
- AL-Mahmoudy, Amany M. M.,AlAwad, Mohammed A.,Alhakamy, Nabil A.,Asfou, Hani Z.,Bokhti, Riham M.,Ibrahim, Tarek S.,Khayya, Ahdab N.,Malebar, Azizah M.,Mohamed, Mamdouh F. A.,Panda, Siva S.,Samir, Ebtihal,Seliem, Israa A.,Tahe, Ehab S.
-
-
- Ligand-free Cu(ii)-catalyzed aerobic etherification of aryl halides with silanes: An experimental and theoretical approach
-
Owing to their wide occurrence in nature and immense applications in various fields, the synthesis of aryl alkyl ethers has remained a focus of interest. In contrast to the conventional/traditional methods of etherification, herein, we have reported a more efficient method, which is better yielding and more general in application. The etherification of aryl halides by alkoxy/phenoxy silanes was catalyzed by copper acetate in the presence of cesium carbonate and oxygen in DMF at 145 °C. All the as-synthesized compounds were characterized via the 1H-NMR and 13C-NMR spectroscopic techniques. Density functional theory calculations using the B3LYP functional were performed to elucidate the reaction mechanism. The C-O coupling reaction between 2-nitroiodobenzene and tetramethoxysilane was used as a model reaction. The activation energy barriers for the generation of catalytic species (31.6 kcal mol-1) and the σ-bond metathesis (16.0 kcal mol-1), oxidative addition/reductive elimination (20.3 kcal mol-1), halogen atom transfer (19.2 kcal mol-1) and single electron transfer (SET) (29.5 kcal mol-1) mechanisms for the C-O coupling reaction were calculated. Calculations for the key reaction steps were repeated with the B3PW91, PBEH1PBE, wB97XD, CAM-B3LYP and mPW1LYP functionals. The formation of catalytic species via a single electron transfer reaction between tetramethoxysilane and copper acetate, formation of methoxy radicals and methoxylation of copper showed an overall energy barrier of 31.6 kcal mol-1, and therefore is the rate determining step.
- Ahmed, Muhammad Naeem,Ahmad, Khalil,Yasin, Khawaja Ansar,Farooq, Tayyaba,Khan, Bilal Ahmad,Roy, Soumendra K.
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p. 11316 - 11333
(2019/07/31)
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- Phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts
-
In this communication, an interesting phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts has been reported. At room temperature and under CO pressure, moderate to good yields of the desired esters can be produced in the absence of bases or an
- Xu, Jian-Xing,Franke, Robert,Wu, Xiao-Feng
-
supporting information
p. 6180 - 6182
(2018/09/10)
-
- Method for preparing ibrutinib
-
The invention discloses a method for preparing ibrutinib. The method includes the following steps of 1, preparation of IB-A, 2, preparation of IB-B, 3, preparation of IB-C, 4, preparation of IB-D, 5,preparation of IB-E, 6, preparation of IB-F, 7, preparation of IB-G, 8, preparation of IB-H, and 9, preparation of IB-J. The method has the advantages that the process is mature and stable, the quality of the product is stable, the production process is safe and reliable, and the ibrutinib is suitable for industrial production.
- -
-
Paragraph 0037-0040; 0078; 0116
(2018/03/26)
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- Highly efficient heterogeneous copper-catalysed O-arylation of phenols by nitroarenes leading to diaryl ethers
-
The heterogeneous O-arylation of phenols by nitroarenes was achieved in DMF at 100 °C by using an MCM-41-immobilised bidentate nitrogen copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst, yielding a variety of unsymmetrical diaryl ethers in good to excellent yields. This heterogeneous copper catalyst can be easily prepared by a simple procedure from commercially readily available and inexpensive reagents, recovered by filtration of the reaction solution and recycled at least seven times without significant loss of activity.
- Du, Yingying,Yao, Fang,Tuo, Yuxin,Cai, Mingzhong
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p. 725 - 729
(2018/01/08)
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- Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings
-
Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.
- Zhai, Yuntong,Chen, Xiaofei,Zhou, Wei,Fan, Mengyang,Lai, Yisheng,Ma, Dawei
-
p. 4964 - 4969
(2017/05/12)
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- INHIBITOR OF BRUTON'S TYROSINE KINASE
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Provided are a compound represented by formula (III) or pharmaceutically acceptable salts, solvates, active metabolites, polymorphs, esters, tautomers or prodrugs thereof, pharmaceutical compositions containing the compound represented by formula (III), and the application of the pharmaceutical compositions as selective inreversible inhibitor of Bruton's tyrosine kinase for the prevention and treatment of inflammation, autoimmune diseases (such as rheumatoid arthritis) associated with aberrant B cell proliferation and cancers.
- -
-
Paragraph 0118; 0119; 0120
(2017/03/28)
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- Metal-free, room-temperature, radical alkoxycarbonylation of aryldiazonium salts through visible-light photoredox catalysis
-
The first radical alkoxycarboxylation of aryldiazonium salts using CO gas through visible-light-induced photoredox catalysis (16 W blue LEDs) has been developed. This reaction is entirely metal-free, is carried out at room temperature with a low loading of an organic dye as a photocatalyst (0.5 mol%), and provides a wide range of arylcarboxylic acid esters in high yields. Importantly, this photocatalytic system can be successfully extended to other carboxylation reactions.
- Guo, Wei,Lu, Liang-Qiu,Wang, Yue,Wang, Ya-Ni,Chen, Jia-Rong,Xiao, Wen-Jing
-
supporting information
p. 2265 - 2269
(2015/02/19)
-
- A counteranion triggered arylation strategy using diaryliodonium fluorides
-
A mild and transition metal-free counteranion triggered arylation strategy has been developed using diaryliodonium fluorides. The fluoride counteranion within the hypervalent iodonium species displays unusual reactivity that activates a phenolic O-H bond leading to electrophilic O-arylation. A wide range of phenols and diaryliodonium salts are compatible with this transformation under remarkably mild conditions. Furthermore, we pre-empt the wider implications of this strategy by demonstrating the compatibility of the arylation tactic with latent carbon nucleophiles.
- Chan,McNally,Toh,Mendoza,Gaunt
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p. 1277 - 1281
(2015/02/05)
-
- Aryl amide small-molecule inhibitors of microRNA miR-21 function
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MicroRNAs (miRNAs) are single stranded RNA molecules of ~22 nucleotides that negatively regulate gene expression. MiRNAs are involved in fundamental cellular processes, such as development, differentiation, proliferation, and survival. MiRNA misregulation has been linked to various human diseases, most notably cancer. MicroRNA-21 (miR-21), a well-established oncomiR, is significantly overexpressed in many types of human cancers, thus rendering miR-21 a potential therapeutic target. Using a luciferase-based reporter assay under the control of miR-21 expression, a high-throughput screen of >300,000 compounds led to the discovery of a new aryl amide class of small-molecule miR-21 inhibitors. Structure-activity relationship (SAR) studies resulted in the development of four aryl amide derivatives as potent and selective miR-21 inhibitors. The intracellular levels of various miRNAs in HeLa cells were analyzed by qRT-PCR revealing specificity for miR-21 inhibition over other miRNAs. Additionally, preliminary mechanism of action studies propose a different mode of action compared to previously reported miR-21 inhibitors, thus affording a new chemical probe for future studies.
- Naro, Yuta,Thomas, Meryl,Stephens, Matthew D.,Connelly, Colleen M.,Deiters, Alexander
-
supporting information
p. 4793 - 4796
(2015/10/28)
-
- Chemoselective and ligand-free synthesis of diaryl ethers in aqueous medium using recyclable alumina-supported nickel nanoparticles
-
An economical and eco-compatible ligand-free protocol for the synthesis of diaryl ethers has been developed using easily accessible alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst in aqueous medium along with a surfactant (SDS) and a mild base (K2CO3). Various sensitive functional groups like allyl, alkoxycarbonyl, formyl, oxo, chloro, bromo, amine and nitro were tolerated in the aforesaid method. Excellent chemoselectivity was demonstrated through competition experiments.
- Ghatak, Avishek,Khan, Sagar,Roy, Rimi,Bhar, Sanjay
-
supporting information
p. 7082 - 7088
(2015/02/02)
-
- INHIBITORS OF BRUTON'S TYROSINE KINASE
-
The invention provides novel poly-substituted 5-membered heterocyclic compounds represented by Formula (IV), or a pharmaceutically acceptable salt, solvate, metabolites, polymorph, ester, tautomer or prodrug thereof, and a composition comprising these compounds. The compounds provided can be used as selective irreversible bruton's tyrosine kinase (Btk) inhibitors and is further useful to treat inflammatory, auto immune diseases associated with aberrant B-cell proliferation such as RA (rheumatoid arthritis) and cancers. This invention also provided the preparation of a medicament using of Formula (IV), and methods of preventing or treating diseases associated with excessive Btk activity in mammals, especially humans. Formula (IV)
- -
-
Paragraph 0379; 0382
(2014/06/23)
-
- NEW COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
-
This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1) wherein R1, R2, R4, R6, E, n, Y1, Y2, Y3, Y4, Y5, L, B, R8, and m are as defined in the claims.
- -
-
Paragraph 0677-0678
(2013/10/22)
-
- Zinc-catalyzed oxidative esterification of aromatic aldehydes
-
A general and efficient protocol for the oxidative esterification of aldehydes has been developed. By using 10 mol % of ZnBr2 and 4 equiv of H2O2, 21 examples of esters were produced in good to excellent yields. Both electron-donating and electron-withdrawing functional groups are tolerable under our reaction conditions.
- Wu, Xiao-Feng
-
experimental part
p. 3397 - 3399
(2012/07/30)
-
- NEW COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
-
This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1) wherein R1, R2, R4, R6, E, n, Y1, Y2, Y3, Y4, Y5, L, B, R8, and m are as defined in the claims.
- -
-
Page/Page column 93
(2012/06/30)
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- Efficient palladium-catalyzed coupling reactions of aryl bromides and chlorides with phenols
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A convenient and general palladium-catalyzed coupling reaction of aryl bromides and chlorides with phenols was developed. Various functional groups such as nitriles, aldehydes, ketones and esters are well tolerated and the corresponding products are obtained in good to excellent yield.
- Hu, Tongjie,Schulz, Thomas,Torborg, Christian,Chen, Xiaorong,Wang, Jun,Beller, Matthias,Huang, Jun
-
supporting information; scheme or table
p. 7330 - 7332
(2010/06/14)
-
- (2-Pyridyl)acetone-promoted Cu-catalyzed O-arylation of phenols with aryl iodides, bromides, and chlorides
-
(Chemical Equation Presented) Employing (2-pyridyl)acetone as a new supporting ligand, the copper-catalyzed coupling reactions of aryl chlorides, aryl bromides, and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. This reaction displays great functional groups compatibility and excellent reactive selectivity.
- Zhang, Qi,Wang, Deping,Wang, Xianyang,Ding, Ke
-
supporting information; experimental part
p. 7187 - 7190
(2009/12/09)
-
- Glyoxal bis(phenylhydrazone) as promoter for CuI-catalyzed O-arylation of phenols with bromoarenes
-
A very simple bishydrazone-type ligand, glyoxal bis(phenylhydrazone) (L1), was found to effectively promote the CuI-catalyzed O-arylation of phenols with aryl bromides. This cross-coupling reaction proceeded in acetonitrile at 60-80 °C in the presence of K3PO4 as base. A diverse array of phenols and bromoarenes was employed as substrates to afford diaryl ethers in good to excellent yields, and some base-sensitive groups, such as ester, aldehyde, and ketone groups, can survive under the mild reaction conditions.
- Liu, Yu-Hua,Li, Gang,Yang, Lian-Ming
-
experimental part
p. 343 - 346
(2009/04/19)
-
- Synthesis, antitubercular activity and docking study of novel cyclic azole substituted diphenyl ether derivatives
-
The re-emergence of tuberculosis (TB) as a global health problem over the past few decades, accompanied by the rise of drug-resistant strains of Mycobacterium tuberculosis, emphasizes the need for discovery of new therapeutic drugs against this disease. The emerging serious problem both in terms of TB control and clinical management prompted us to synthesize a novel series of heterocyclic o/m/p substituted diphenyl ether derivatives and determine their activity against H37Rv strain of Mycobacterium. All 10 compounds inhibited the growth of the H37Rv strain of mycobacterium at concentrations as low as 1 μg/mL. This level of activity was found comparable to the reference drugs rifampicin and isoniazid at the same concentration. Molecular modeling of the binding of the diphenyl ether derivatives on enoyl-ACP reductase, the molecular target site of triclosan, indicated that these compounds fit within the binding domain occupied by triclosan. Hence the diphenyl ether derivatives tested in this study were docked to ENR and the binding of the diphenyl ether derivatives was also estimated using a variety of scoring functions that have been compiled into the single consensus score. As the scores ranged from 47.27% to 65.81%, these bioactive compounds appear to have a novel mechanism of action against M. tuberculosis, and their structural features should be studied further for their potential use as new antitubercular drugs.
- Kini, Suvarna G.,Bhat, Anilchandra R.,Bryant, Byron,Williamson, John S.,Dayan, Franck E.
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experimental part
p. 492 - 500
(2009/08/07)
-
- Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers
-
A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.
- Aranyos, Attila,Old, David W.,Kiyomori, Ayumu,Wolfe, John P.,Sadighi, Joseph P.,Buchwald, Stephen L.
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p. 4369 - 4378
(2007/10/03)
-
- Mechanisms of the photochemical rearrangement of diphenyl ethers
-
The mechanism of the photochemical rearrangement of diphenyl ether (1a) was studied. Irradiation of 1a in ethanol gave 2-phenylphenol (2, 42%) and 4-phenylphenol (3, 11%) as rearrangement products, in addition to phenol (4, 30%) and benzene (5, 25%) as diffusion products. Cross-coupling experiments employing [2H10]1a demonstrated that the formation of 2- and 4-phenylphenol was an intramolecular process. Irradiation of 1a in benzene or in toluene gave biphenyls in good yields. The combined yields of rearrangement products (2 and 3) increased with increase of solvent viscosity, with a concomitant decrease in the formation of 4. All the results can be rationalized in terms of excitation of 1a to the singlet state and dissociation to a radical pair intermediate involving phenoxy and phenyl radicals. Intramolecular recombination of these radicals gives rearrangement products, and escape followed by hydrogen abstraction from the solvent gives diffusion products. When position 4 of 1a was occupied by an electron-donating substituent (1b-e), aryloxy-phenyl bond cleavage to give the corresponding rearrangement products prevailed over phenoxy-aryl bond cleavage. The opposite was the case for substrates with an electron-withdrawing substituent at position 4 (1h,i).
- Haga, Naoki,Takayanagi, Hiroaki
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p. 735 - 745
(2007/10/03)
-
- A NOVEL, SIMPLE METHOD FOR THE PREPARATION OF HINDERED DIPHENYL ETHERS
-
The displacement of the nitro group from substituted nitrobenzenes is used for the synthesis of diphenyl ethers. 1,4-Dinitrobenzene has been converted into a variety of hindered diphenyl ethers using 2,6-disubstituted phenoxides and studies show that the mechanism of formation of the ether (5a) is radical in nature.
- Sammes, Peter G.,Thetford, Dean,Voyle, Martyn
-
p. 3229 - 3232
(2007/10/02)
-
- Displacement of an Aromatic Nitro Group using Phenoxides
-
1,4-dinitrobenzene undergoes nucleophilic substitution with sodium phenoxide and several hindered 2,6-disubstituted phenoxides to afford diphenyl ethers.
- Sammes, P. G.,Thetford, D.,Voyle, M.
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p. 1373 - 1374
(2007/10/02)
-
- THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS. PART X. STUDIES ON THE PHENYLATION AND OXIDATION OF PHENOLS
-
The influence of the substituents on the phenol on the regiochemistry of the arylation reactions with Ph3BiCl2 and other bismuth reagents has been studied.O-Phenylation occurs with phenols substituted with electron-withdrawing groups.Electron-donating substituted phenols undergo ortho C-phenylation.Oxidative dimerisation has been observed with 2,6-dialkyl phenols.
- Barton, Derek H. R.,Yadav-Bhatnagar, Neerja,Finet, Jean-Pierre,Khamsi, Jamal,Motherwell, William B.,Stanforth, Stephen P.
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p. 323 - 332
(2007/10/02)
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- COPPER CATALYSED O-PHENYLATION OF PHENOLS AND ENOLS BY PENTAVALENT ORGANOBISMUTH COMPOUNDS
-
The O-phenylation of phenols under neutral conditions by Bi(V) reagents is strongly catalysed by copper salts and by copper powder, even at room temperature.Enolic systems are also subject to copper powder catalysis and give exclusively O-phenylation.
- Barton, Derek H. R.,Finet, Jean-Pierre,Khamsi, Jamal,Pichon, Clotilde
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p. 3619 - 3622
(2007/10/02)
-
- Analogues of clofibrate and clobuzarit containing fluorine in the side chains
-
A series of analogues of clofibrate and 2-[4-(4-chlorophenyl)phenylmethoxy]-2-methylpropionic acid (clobuzarit) has been prepared by replacing the methyl groups by trifluoromethyl groups and changing the aromatic moiety. The activity of these compounds has been assayed on the plasma levels of cholesterol, Total Esterified Fatty Acids (T.E.F.A.) and fibrinogen in rats. It appears that derivatives of the first series which contain only one trifluoromethyl group are hypocholesterolaemic and that many mono- of bis- trifluoromethyl derivatives of the second series lower the levels of both cholesterol and T.E.F.A. in contrast to clobuzarit.
- Haydock,Mulholland,Telford,et al.
-
p. 205 - 214
(2007/10/02)
-