- Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source
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An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.
- Dogga, Bhushanarao,Joseph, Jayan T.,Kumar, C. S. Ananda
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supporting information
p. 309 - 313
(2020/12/23)
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- Palladium-Catalyzed Synthesis of N, N-Dimethylanilines via Buchwald-Hartwig Amination of (Hetero)aryl Triflates
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This work delineates the synthesis of N,N-dimethylaniline derivatives from dimethylamines and aryl triflates. The palladium-catalyzed C-N bond formation proceeds in excellent yields, using an unsophisticated catalytic system, a mild base, and triflates as electrophiles, which are readily available from inexpensive phenols. N,N-Dimethylanilines are multifunctional reaction partners and represent useful but underutilized building blocks in organic synthesis.
- Pospech, Jola,Taeufer, Tobias
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p. 7097 - 7111
(2020/06/27)
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- Palladium-Catalyzed Cyclobutanation of Aryl Sulfonates through both C-O and C-H Cleavage
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A palladium-catalyzed cyclobutanation of aryl sulfonates with strained alkenes has been developed. The methodology is featured to achieve the cleavage of both C-O and C-H bonds of phenol derivatives in one pot. Under the reaction conditions, in addition t
- Zhang, Liangwei,Liu, Long,Huang, Tianzeng,Dong, Qizhi,Chen, Tieqiao,Chen, Tieqiao
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p. 2189 - 2196
(2020/06/05)
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- Design, Synthesis, and Structure-Activity Relationships of Indoline-Based Kelch-like ECH-Associated Protein 1-Nuclear Factor (Erythroid-Derived 2)-Like 2 (Keap1-Nrf2) Protein-Protein Interaction Inhibitors
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The Keap1 (Kelch-like ECH-associated protein 1)-Nrf2 (nuclear factor erythroid 2-related factor 2)-ARE (antioxidant response element) pathway is the major defending mechanism against oxidative stresses, and directly disrupting the Keap1-Nrf2 protein-protein interaction (PPI) has been an attractive strategy to target oxidative stress-related diseases, including cardiovascular diseases. Here, we describe the design, synthesis, and structure-activity relationships (SARs) of indoline-based compounds as potent Keap1-Nrf2 PPI inhibitors. Comprehensive SAR analysis and thermodynamics-guided optimization identified 19a as the most potent inhibitor in this series, with an IC50 of 22 nM in a competitive fluorescence polarization assay. Further evaluation indicated the proper drug-like properties of 19a. Compound 19a dose-dependently upregulated genes and protein level of Nrf2 as well as its downstream markers and showed protective effects against lipopolysaccharide-induced injury in both H9c2 cardiac cells and mouse models. Collectively, we reported here a novel indoline-based Keap1-Nrf2 PPI inhibitor as a potential cardioprotective agent.
- Zhou, Hai-Shan,Hu, Lv-Bin,Zhang, Han,Shan, Wen-Xin,Wang, Yan,Li, Xue,Liu, Tian,Zhao, Jing,You, Qi-Dong,Jiang, Zheng-Yu
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supporting information
p. 11149 - 11168
(2020/11/09)
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- First Study of the Thermal and Storage Stability of Arenediazonium Triflates Comparing to 4-Nitrobenzenediazonium Tosylate and Tetrafluoroborate by Calorimetric Methods
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Herein, for the first time, using isothermal flow calorimetry and differential scanning calorimetry (DSC)/thermal gravimetric analysis (TGA), we have determined the thermal decomposition energies for the number of solid arenediazonium triflates comparing to 4-nitrobenzene tosylate and 4-nitrobenzentetrafluoroborate. The kinetics of thermal decomposition, activation energies, and half-lives of the studied diazonium salts (DSs) were found. Using gas chromatography-mass spectrometry (MS) and liquid chromatography-MS, we have elucidated the products formed during thermolysis of the investigated DSs. By density functional theory quantum chemical calculations at the B3LYP/aug-cc-pVDZ level of theory, we simulated the thermodynamics of decomposition reactions proceeding via substitution of the diazonium group by corresponding nucleophiles. The method applied predicted the decomposition energies of all the studied compounds fairly precise, except for 2-nitrobenzene diazonium triflate. It has been found that 4-nitrobenzene diazonium triflate has increased storage stability under normal conditions comparing to the corresponding tosylate and tetrafluoroborate. The experimental and theoretical results demonstrated that comparing to DSC/TGA, isothermal flow calorimetry more adequately reflects the energetics of the thermal decomposition of DSs and their storage stability under normal conditions.
- Bondarev, Alexander A.,Naumov, Evgeny V.,Kassanova, Assiya Zh.,Krasnokutskaya, Elena A.,Stankevich, Ksenia S.,Filimonov, Victor D.
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p. 2405 - 2415
(2019/10/11)
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- Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers
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By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-l-thyronine (3-T1) derivative was synthesized by this aryl migration procedure.
- Chen, Huangguan,Han, Jianwei,Wang, Limin
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p. 12313 - 12317
(2018/09/10)
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- Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres
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A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include α-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.
- Scheidt, Felix,Neufeld, Jessica,Sch?fer, Michael,Thiehoff, Christian,Gilmour, Ryan
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supporting information
p. 8073 - 8076
(2019/01/04)
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- Directed ortho Metalation (D o M)-Linked Corriu-Kumada, Negishi, and Suzuki-Miyaura Cross-Coupling Protocols: A Comparative Study
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A systematic study of the widely used, titled name reaction transition-metal-catalyzed cross-coupling reactions with attention to context with the directed ortho metalation (D o M) is reported. In general, the Suzuki-Miyaura and Negishi protocols show gre
- Quesnelle, Claude A.,Snieckus, Victor
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supporting information
p. 4395 - 4412
(2018/11/21)
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- Palladium nanoparticles: Chemoselective control for reductive Heck with aryl triflates and 2,3-dihydrofuran
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The reductive-Heck reaction offers a unique entry to formal Csp2-Csp3 cross-coupling reactions that proceed in the absence of a main group organometallic coupling partner. Consequently, further development of new variants would be transformative. Unfortunately, controlling the relative rates of the organopalladium intermediates has proven difficult with homogenous, single-site Pd catalysts. This work describes a selective reductive Heck reaction catalyzed by Pd-nanoparticles. The reaction works well with electron-deficient aryl triflates at room temperature in the absence of ligands. This work addresses some of the challenges found in the reductive-Heck literature.
- Rosas Vargas, Daisy,Cook, Silas P.
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supporting information
p. 3314 - 3317
(2018/05/04)
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- Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
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Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
- Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
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p. 5025 - 5038
(2017/10/06)
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- Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates
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Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.
- Huang, He,Wu, Yang,Zhang, Wen,Feng, Chun,Wang, Bi-Qin,Cai, Wan-Fei,Hu, Ping,Zhao, Ke-Qing,Xiang, Shi-Kai
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p. 3094 - 3101
(2017/03/23)
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- Copper-Catalyzed Enantioselective 1,6-Boration of para-Quinone Methides and Efficient Transformation of gem-Diarylmethine Boronates to Triarylmethanes
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Presented is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides. The reaction proceeds with excellent yields and good to excellent enantioselectivities, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters. Additionally, the subsequent conversion of the derived potassium trifluoroborates into triarylmethanes with highly enantiospecificity was realized.
- Lou, Yazhou,Cao, Peng,Jia, Tao,Zhang, Yongling,Wang, Min,Liao, Jian
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supporting information
p. 12134 - 12138
(2015/10/12)
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- Regioselectivity switch achieved in the palladium catalyzed α-arylation of enones by employing the modified Kuwajima-Urabe conditions
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A new regioselective approach to the synthesis of α-aryl enones is reported. This represents an important application of the Kuwajima-Urabe protocol toward the synthesis of this simple albeit complex functional array. Several α-aryl enones were synthesized by the palladium catalyzed arylation of triethylsilylenol ethers of enones with high regioselectivity and broad scope, utilizing sterically encumbered electron-rich phosphine ligands to drive the reaction.
- Kale, Ajit Prabhakar,Pawar, Govind Goroba,Kapur, Manmohan
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supporting information; experimental part
p. 1808 - 1811
(2012/06/18)
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- Palladium-catalyzed desulfitative arylation by C-O bond cleavage of aryl triflates with sodium arylsulfinates
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An efficient Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates as arylation reagents by C-O bond cleavage of aryl triflates was developed. With only 2 mol % of Pd(OAc)2 as catalyst and XPhos as ligand, the reaction proceeded well for a range of substrates.
- Zhou, Chao,Liu, Qingjiang,Li, Yaming,Zhang, Rong,Fu, Xinmei,Duan, Chunying
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p. 10468 - 10472
(2013/01/15)
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- Biaryl and aryl ketone synthesis via Pd-catalyzed decarboxylase coupling of carboxylate salts with aryl triflates
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A bimetallic catalyst system has been developed that for the first time allows the decarboxylative crosscoupling of aryl and acyl carboxylates with aryl triflates. In contrast to aryl halides, these electrophiles give rise to non-coordinating anions as byproducts, which do not interfere with the decarboxylation step that leads to the generation of the carbon nucleophilic crosscoupling partner. As a result, the scope of carboxylate substrates usable in this transformation was extended from ortho-substituted or otherwise activated derivatives to a broad range of ortho-, meta-, and para-substituted aromatic carboxylates. Two alternative protocols have been optimized, one involving heating the substrates in the presence of CuI/1,10- phenanthroline (10-15 mol %) and PdI2/phosphine (23 mol%) in NMP for 1-24 h, the other involving CuI/l,10-phenanthroline (615mol%) and PdBr2/Tol-BINAP (2 mol % ) in NMP using microwave heating for 5-10 min. While most products are accessible using standard heating, the use of microwave irradiation was found to be beneficial especially for the conversion of non-activated carboxylates with functionalized aryl triflates. The synthetic utility of the transformation is demonstrated with 48 examples showing the scope and limitations of both protocols. In mechanistic studies, the special role of microwave irradiation is elucidated, and further perspectives of decarboxylase crosscouplings are discussed.
- Goossen, Lukas J.,Linder, Christophe,Rodriguez, Nuria,Lange, Paul P.
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supporting information; experimental part
p. 9336 - 9349
(2010/04/03)
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- Direct synthesis of primary arylamines via C-N cross-coupling of aryl bromides and triflates with amides
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Aryl halides and triflates are coupled with primary amides to give the corresponding arylamines in the presence of a palladium catalyst, a suitable ligand, and a base. The catalyst system performs well for a large number of different substrates at 100-150 °C without solvent, and with low catalyst levels (0.12 mol % Pd). Nicotinamide might be useful as a nitrogen source in the Pd-catalyzed amination reaction.
- Romero,Harrak,Basset,Orúe,Pujol
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experimental part
p. 1951 - 1956
(2009/07/11)
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- Aryl triflates: Useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C-H activation-functionalization
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Aryl triflates were found to be suitable partners for the palladium catalyzed direct arylation of heteroaromatics via C-H activation- functionalization. The reaction conditions and the catalyst have a determining influence on the yields. The system combining PPh3 and Pd(OAc) 2 using KOAc as base and DMF as solvent promotes the selective 2- or 5-arylations in moderate to high yields. Several heteroaromatics such as furan, thiophene, thiazole or oxazole derivatives have been employed successfully. The electronic properties of the aryl triflates also have a decisive influence on the yields of the coupling products. Electron-rich aryl triflates gave satisfactory results, whereas the electron-poor ones led to the formation of phenols. The Royal Society of Chemistry 2008.
- Roger, Julien,Doucet, Henri
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p. 169 - 174
(2008/09/20)
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- Fragment-based substrate activity screening method for the identification of potent inhibitors of the Mycobacterium tuberculosis phosphatase PtpB
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A new substrate-based fragment approach for the identification of novel PTP inhibitors is presented. This method was applied to Mycobacterium tuberculosis PtpB, a promising new target for the treatment of tuberculosis. This resulted in the development of the most potent PtpB inhibitor reported to date (0.22 μM) with low molecular weight and good selectivity against a panel of other protein tyrosine phosphatases. Copyright
- Soellner, Matthew B.,Rawls, Katherine A.,Grundner, Christoph,Alber, Tom,Ellman, Jonathan A.
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p. 9613 - 9615
(2008/02/13)
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- Heterogeneous Pd/C-catalyzed ligand-free, room-temperature suzuki-miyaura coupling reactions in aqueous media
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A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector ( 1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis.
- Maegawa, Tomohiro,Kitamura, Yoshiaki,Sako, Satoko,Udzu, Takahiro,Sakurai, Ai,Tanaka, Asami,Kobayashi, Yusuke,Endo, Koichi,Bora, Utpal,Kurita, Takanori,Kozaki, Atsushi,Monguchi, Yasunari,Sajiki, Hironao
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p. 5937 - 5943
(2008/02/13)
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- A polystyrene-supported triflating reagent for the synthesis of aryl triflates
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An insoluble polystyrene-supported triflating reagent has been prepared by suspension co-polymerization of N-(4-vinylphenyl)trifluoromethanesulphonimide, styrene and the JandaJel cross-linker. This reagent, in the presence of triethylamine, allows for the efficient synthesis of aryl triflates from a wide range of phenols in a process that permits the desired product to be isolated from the reaction mixture in essentially pure form via several filtration and concentration operations. Adding to the utility of this reagent is its ability to be easily recovered, regenerated and reused. Both soluble and insoluble bifunctional polymers containing trialkylamine moieties in addition to triflimide groups were also prepared and examined as triflating reagents. Unfortunately these reagents afforded only modest yields of the desired products in representative reactions. Graphical Abstract.
- Chung, Cecilia Wan Ying,Toy, Patrick H.
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p. 709 - 715
(2007/10/03)
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- The sequel to a carbocyclic nucleoside synthesis: A divergent access to both arenediazonium ions and aryl triflates
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Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration.
- Picherit,Wagner,Uguen
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p. 2579 - 2583
(2007/10/03)
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- Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
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Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.
- Seganish, W. Michael,DeShong, Philip
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p. 1137 - 1143
(2007/10/03)
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- FUNGAL CELL WALL SYNTHESIS GENE
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A reporter system reflecting the transport process that transports GPI-anchored proteins to the cell wall was constructed and compounds inhibiting this process were discovered. Further, genes conferring resistance to the above compounds were identified and methods of screening for compounds that inhibit the activity of the proteins encoded by these genes were developed.Therefore, through the novel compounds, the present invention showed that antifungal agents having a novel mechanism, i.e. inhibiting the process that transports GPI-anchored proteins to the cell wall, could be achieved.
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- Methods of treating insulin resistance syndrome and diabetes
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This invention is directed to methods of treating insulin resistance syndrome and diabetes in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound derived from adenosine and analogues thereof, or a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof, or a pharmaceutical composition comprising such compound.
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- Palladium-catalyzed phosphination of functionalized aryl triflates
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Catalytic user-friendly approach to the syntheses of various functionalized aromatic phosphines from their corresponding substituted aryl triflates and triarylphosphines was accomplished. This method is carried out in neutral media and compatible with man
- Kwong, Fuk Yee,Lai, Chi Wai,Yu, Michael,Tian, Yuan,Chan, Kin Shing
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p. 10295 - 10305
(2007/10/03)
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- Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties
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A compound of the formula wherein K is N; Q is CH2or O; R6is hydrogen, alkyl, allyl, 2-methylallyl, 2-butenyl, or cycloalkyl where the nitrogen of the ring of X is substituted by Y; E is O or S; Y is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, or substituted heterocyclylalkyl; and n and p are independently 0, 1, 2, or 3, provided that n+p is at least 1; T is hydrogen, alkyl, alkylcarbonyl, alkylthiocarbonyl, halo, carboxyl, A and B are independently hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, or OR′; or a pharmaceutically acceptable salt thereof, a pharmaceutic-ally acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof.
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- Hypervalent silane and siloxane derivatives and the use thereof
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Hypervalent silane and siloxane reagents (preformed or generated in situ) for transmetalation in palladium catalyzed reactions with derivatives of allylic alcohols, aryl halides, electron-withdrawing aryl bromides, and aryl triflates derived from phenols are disclosed. Also disclosed are methods of preparing glycosyl azides by reaction of an azide with a silyl ester in the presence of a phoshine.
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- Practical Synthesis of Aryl Triflates under Aqueous Conditions
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A practical and efficient synthesis of aryl triflates under biphasic basic aqueous conditions is described. The current methodology provides entry into these valuable substrates that omits the use of amine bases and allows facile isolation by s
- Frantz, Doug E.,Weaver, Damian G.,Carey, James P.,Kress, Michael H.,Dolling, Ulf H.
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p. 4717 - 4718
(2007/10/03)
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- Synthesis of unsymmetrical biaryls by palladium-catalyzed cross coupling reactions of arenes with tetrabutylammonium triphenyldifluorosilicate, a hypervalent silicon reagent
-
Palladium-catalyzed cross coupling of arenes with tetrabutylammonium triphenyldifluorosilicate, a hypervalent silicon reagent, to give unsymmetrical biaryls is reported. The Pd(0)-catalyzed process proceeds in good yield with aryl iodides, most aryl trifiates, and electron-deficient aryl bromides.
- Mowery, Molly E.,DeShong, Philip
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p. 3266 - 3270
(2007/10/03)
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- A facile route to aryl amines: Nucleophilic substitution of aryl triflates
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The aromatic nucleophilic substitution (S(N)Ar) between aryl triflates and secondary amines has been studied. In the absence of solvent, the reaction proceeds at room temperature for nitro and cyano activated aryl triflates and requires higher temperatures in the case of carboxy activation. Variable triflate reactivity could be explained in terms of frontier molecular orbital theory. This methodology has been applied for the synthesis of substituted piperidyl pyridines.
- Schio, Laurent,Lemoine, Guy,Klich, Michel
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p. 1559 - 1562
(2007/10/03)
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- 4-Nitrophenyltriflate as a New Triflating Agent
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Aryl triflates were prepared under mild conditions using 4-nitrophenyl triflate (1) as a stable, crystalline triflating agent.
- Zhu, Jieping,Bigot, Antony,Elise, Marie,Dau, Tran Huu
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p. 1181 - 1182
(2007/10/03)
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- Cross-coupling reaction of pentacoordinate alkenylsilicates with organic halides and triflates catalyzed by a palladium complex
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Isolated pentacoordinate alkoxy-substituted alkenylsilicates, are readily prepared by mixing alkenyltrialkoxysilane, catechol and triethylamine at room temperature.Cross-coupling reactions of these alkenylsilicates with organic halides or triflates are catalyzed by a palladium complex and proceed very smoothly and cleanly to give the corresponding alkenes.The cross-coupling reactions could be also attained by a one pot operation without isolation of pentacoordinate organosilicates.The mechanism of this cross-coupling reaction is also described here. alkoxy-substituted alkenylsilicate / pentacoordinate silicate / cross-coupling / palladium catalyst / aryl halide / aryl triflate / styrene derivative / 1,3-diene
- Hojo, Makoto,Murakami, Chikara,Aihara, Hidenori,Komori, Ei-ichi,Kohra, Shinya,et al.
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p. 499 - 508
(2007/10/02)
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- A Facile Preparation of Aryl Triflates. Decomposition of Arenediazonium Tetrafluoroborate Salts in Trifluoromethanesulfonic Acid
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The thermal or photochemical decomposition of arenediazonium tetrafluoroborate salts n trifluoromethanesulfonic acid, with or without organic bases such as pyridine, provides aryl triflates in high yields.
- Yoneda, Norihiko,Fukuhara, Tsuyoshi,Mizokami, Takao,Suzuki, Akira
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p. 459 - 460
(2007/10/02)
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- High pressure organic chemistry; XI. A new convenient synthesis of aromatic amines from activated phenols
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Aryl triflates containing electron-withdrawing substituents efficiently react with amines in refluxing acetonitrile or at 10 kbar pressure to give various aromatic amines.
- Kotsuki,Kobayashi,Suenaga,Nishizawa
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p. 1145 - 1147
(2007/10/02)
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- SYNTHESIS OF DIARYLIC COMPOUNDS BY PALLADIUM CATALYZED REACTION OF AROMATIC TRIFLATES WITH BORONIC ACIDS
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The known triflates 3c-5c react with the boronic acid 2j to produce the known biarylic compounds 3j-5j.An extension of this new procedure by reacting the novel triflate 1c with the arylboronic acids 2f-j affords the new correspondingly arylated compounds 1f-j.
- Huth, Andreas,Beetz, Ilse,Schumann, Ingrid
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p. 6679 - 6682
(2007/10/02)
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