- Very fast Suzuki-Miyaura reaction catalyzed by Pd(OAc)2 under aerobic conditions at room temperature in EGME/H2O
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The results of a ligand-free Pd(OAc)2-catalyzed Suzuki-Miyaura C-C coupling performed at room temperature under aerobic conditions are presented. It was found that the use of an ethylene glycol monomethyl ether/H2O mixture as the solvent resulted in very rapid reactions of aryl bromides with arylboronic acids. As a matter of fact, under optimized conditions, some substrates were converted quantitatively in less than 1 min with exceptionally high TOF values. For example, the reaction between 4-methoxyphenylboronic acid and bromobenzene afforded 4-methoxybiphenyl in 30 s with TOF = 180000 h-1. Furthermore, the reaction tolerates a wide range of functional groups and can be successfully applied to heteroaryl bromides such as 2-bromopyridine and 5-bromopyrimidine. Interestingly, also an activated aryl chloride such as 1-chloro-4-nitrobenzene reacted quantitatively with phenylboronic acid at 373 K. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Del Zotto, Alessandro,Amoroso, Francesco,Baratta, Walter,Rigo, Pierluigi
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Read Online
- Phosphine-free palladium-catalyzed cross-coupling of tris(1- naphthyl)borane with aryl halides and iodonium salts
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The catalytic cross-coupling reactions of the benzene complex of tris(1- naphthyl)borane with aryl halides and diaryliodonium salts are shown to occur smoothly in aqueous acetone or water in the presence of Na2CO3 or NaOH using PdCl2 as the catalyst precursor and give 1-arylnaphthalenes in high yields.
- Bumagin, Nikolay A.,Tsarev, Dmitriy A.
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Read Online
- 2-subtituted fluorene-based compound, hole transport material including the same, and organic electronic device including the same in a hole transport layer
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The present invention addresses the problems of providing a compound that can be used as a hole transport material having excellent hole injection or transport performance, electron blocking performance, light stability, electrical stability, and thermal stability, providing a hole transport material containing the compound, and an organic electronic device including an organic EL element or an organic photoelectric conversion element provided with a hole transport layer containing the compound, particularly an organic electronic device including an organic EL element having a long lifetime and high luminous efficiency. A compound is represented by general formula (1-1); in the formula, R1 to R6 and Ara to Arc are as defined in the specification.
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Paragraph 0248-0253
(2020/06/30)
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- Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
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The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
- Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
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supporting information
p. 4941 - 4948
(2019/11/03)
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- Nitrogen-containing compound, photoelectric conversion device, and electronic device
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The invention provides a nitrogen-containing compound, a photoelectric conversion device and an electronic device, and belongs to the technical field of photoelectricity. The structural general formula of the nitride-containing compound is shown as a formula I, and Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl with the carbon atom number of 6-30, wherein substituents of Ar1 and Ar2 are the same or different and are independently selected from deuterium, tritium, halogen, cyano, amino, hydroxyl, nitryl, alkyl with the carbon atom number being 1-20, naphthenic base with the carbon atom number being 3-20 and aryl with the carbon atom number being 6-30. According to the nitrogen-containing compound and the photoelectric conversion device, the photoelectric conversion efficiency of the device can be improved, and the service life of the device is prolonged.
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Paragraph 0058; 0061-0062
(2019/12/02)
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- An efficient class of bis-NHC salts: Applications in Pd-catalyzed reactions under mild reaction conditions
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This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.
- Chiu, Chien-Cheng,Chiu, Hui-Tzu,Lee, Dong-Sheng,Lu, Ta-Jung
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p. 26407 - 26415
(2018/08/04)
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- One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
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A methodology for a sequential palladium-catalyzed cross-coupling procedure consisting of borylation, the Suzuki reaction and amination has been developed for the assembly of molecules with multi-aryl backbones. The linchpin of this development is the meta-terarylphosphine ligand, Cy*Phine, which has been employed as an air- and moisture-stable precatalyst, Pd(Cy*Phine)2Cl2, to improve the efficiency of one-pot borylation–Suzuki reactions. Additionally, the reactivity of the Pd-Cy*Phine system could be tuned to furnish a one-pot, borylation–Suzuki reaction–amination (BSA) cross-coupling treble. The methodology successfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74–94% could be achieved for each segment that cumulatively afforded 50–84% yield over the entire three-step sequence in a single pot. (Figure presented.).
- Jong, Howard,Eey, Stanley T.-C.,Lim, Yee Hwee,Pandey, Sangeeta,Iqbal, Nurul Azmah Bte,Yong, Fui Fong,Robins, Edward G.,Johannes, Charles W.
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supporting information
p. 616 - 622
(2017/02/23)
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- Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
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A novel organic compound having a high hole-transport property is provided. A long-lifetime light-emitting element is provided. An organic compound represented by General Formula (G0) is provided. In General Formula (G0), Ar1 represents a substituted or unsubstituted naphthyl group, Ar2 represents a substituted or unsubstituted carbazolyl group, Ar3 represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted spirofluorenyl group, and α1 and α2 each independently represent a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenyldiyl group.
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Page/Page column 69; 70
(2016/09/26)
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- Pd/mannose promoted tandem cross coupling-nitro reduction: Expedient synthesis of aminobiphenyls and aminostilbenes
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The dual role of d-mannose as a ligand for Pd catalyzed cross-coupling, and as a hydrogen source for nitro reduction is demonstrated in a modular cross coupling-nitro reduction sequence. The synthetic utility and generality of this green protocol has been illustrated by the synthesis of 20 aminobiphenyl and 10 aminostilbene derivatives in high yields through a one-pot Suzuki coupling-nitro reduction and a Heck coupling-nitro reduction, respectively, starting from halonitroarenes as substrates.
- Rohilla, Sandeep,Pant, Pradeep,Jain, Nidhi
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p. 31311 - 31317
(2015/04/22)
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- Org. compd.
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To provide a novel anthracene derivative which exhibit blue to blue green light emission, provide a light-emitting element which emits blue to blue green light, provide a light-emitting element which emits blue to blue green light with a long lifetime, and provide a light-emitting element which emits blue to blue green light with high emission efficiency, an anthracene derivative represented by General Formula (G1) is provided. In addition, a light-emitting element which emits blue to blue green light can be obtained by using the anthracene derivatives represented by General Formula (G1). Further, a light-emitting element which emits blue to blue green light with high emission efficiency and/or high reliability can be obtained by using the anthracene derivatives represented by General Formula (G1).
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Paragraph 0306-0308
(2016/10/09)
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- ORGANIC COMPOUND, ANTHRACENE DERIVATIVE, AND LIGHT-EMITTING ELEMENTS, LIGHT-EMITTING DEVICES, ELECTRONIC DEVICES, AND LIGHTING DEVICES USING THE ANTHRACENE DERIVATIVE
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To provide a novel anthracene derivative which exhibit blue to blue green light emission, provide a light-emitting element which emits blue to blue green light, provide a light-emitting element which emits blue to blue green light with a long lifetime, and provide a light-emitting element which emits blue to blue green light with high emission efficiency, an anthracene derivative represented by General Formula (G1) is provided. In addition, a light-emitting element which emits blue to blue green light can be obtained by using the anthracene derivatives represented by General Formula (G1). Further, a light-emitting element which emits blue to blue green light with high emission efficiency and/or high reliability can be obtained by using the anthracene derivatives represented by General Formula (G1).
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- ANTHRACENE DERIVATIVE AND LIGHT-EMITTING DEVICES, ELECTRONIC DEVICES, AND LIGHTING DEVICE USING THE ANTHRACENE DERIVATIVE
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An anthracene derivative is disclosed, and a light-emitting element, a light-emitting device, an electronic device, and a lighting device using the anthracene derivatives are demonstrated. The structure of the anthracene derivative is described in detail in the specification. The use of the anthracene derivative enables the production of a blue emissive light-emitting element having high emission efficiency, excellent purity of emission color, and a long lifetime, which contributes to the production of a high-performance light-emitting device, electronic device, and lighting device.
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Page/Page column 34
(2010/05/13)
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- New cyclopentadienyl, indenyl or fluorenyl substituted phosphine compounds and their use in catalytic reactions
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The invention is directed to a phosphine compound represented by general formula (1) wherein R' and R" independently are selected from alkyl, cycloalkyl and 2-furyl radicals, or R' and R" are joined together to form with the phosphorous atom a carbon-phosphorous monocycle comprising at least 3 carbon atoms or a carbon-phosphorous bicycle; the alkyl radicals, cycloalkyl radicals, and carbon-phosphorous monocycle being unsubstituted or substituted by at least one radical selected from the group of alkyl, cycloalkyl, aryl, alkoxy, and aryloxy radicals; Cps is a partially substituted or completely substituted cyclopentadien-1-yl group, including substitutions resulting in a fused ring system, and wherein a substitution at the 1-position of the cyclopentadien-1-yl group is mandatory when the cyclopentadien-1-yl group is not part of a fused ring system or is part of an indenyl group. Also claimed is the use of these phosphines as ligands in catalytic reactions and the preparation of these phosphines.
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Page/Page column 53; 55; 59
(2008/06/13)
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- 9-Fluorenylphosphines for the Pd-catalyzed Sonogashira, Suzuki, and Buchwald-Hartwig coupling reactions in organic solvents and water
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The lithiation/alkylation of fluorene leads to various 9-alkyl-fluorenes (alkyl = Me. Et, /Pr, -Pr. -C18H25) in > 95% yields, for which lithiation and reaction with R2PCl (R = Cy, iPr, tBu) generates 9-alkyl, 9-PR2fluorenes which constitute electron-rich and bulky phosphine ligands. The in-situ-formed palladium-phosphinc complexes ([Na2PdCl4], phosphonium salt, base, substrates) were tested in the Sonogashira. Suzuki, and Buchwald-Hartwig reactions of aryl chlorides and aryl bromides in organic solvents. The Sonogashira coupling of aryl chlorides at 100-120°C leads to >90% yields with 1 mol % of Pd catalyst. The Suzuki coupling of aryl chlorides typically requires 0.05 mol % of Pd catalyst at 100°C in dioxane for quantitative product formation. To carry out "green" cross-coupling reactions in water, 9-ethylfluorenyldicyclohexylphosphine was reacted in sulphuric acid to generate the respective 2-sulfonated phosphonium salt. The Suzuki coupling of activated aryl chlorides by using this water-soluble catalyst requires only 0.01 mol% of Pd catalyst, while a wide range of aryl chlorides can be quantitatively converted into the respective coupling products by using 0.1-0.5 mol % of catalyst in pure water at 100°C. Difficult substrate combinations, such as naphthylboronic acid or 3-pyridylboronic acid and aryl chlorides are coupled at 100°C by using 0.1-0.5 mol % of catalyst in pure water to obtain the respective N-heterocycles in quantitative yields. The copper-free aqueous Sonogashira coupling of aryl bromides generates the respective tolane derivatives in > 95 % yield.
- Fleckenstein, Christoph A.,Plenio, Herbert
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p. 2701 - 2716
(2008/03/14)
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- NOVEL HETEROCYCLIC AMIDE DERIVATIVES HAVING DIHYDROOROTATE DEHYDROGENASE INHIBITING ACTIVITY
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Novel heterocyclic amide derivatives having pharmacological effects, that is, compounds represented by the general formula (1) or salts thereof: (1) wherein X1-X2 is S-CH2 or the like; R1 is alkyl or the like; p is 0 to 7; R2 is hydrogen, alkyl, or the like; R3 is hydrogen, alkyl, or the like; Y1-Y2 is CH=CH or the like; R4 is halogeno, alkyl, or the like; q is 0 to 4; and R5 is halogeno, hydrogen, alkyl, or the like.
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Page/Page column 51; 53-54
(2010/10/20)
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- Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
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A novel bis-phenanthryl N-heterocyclic carbene (NHC) based palladium acetate catalyst was effective for the coupling of various aryl and vinyl chlorides with organoboron compounds. N,N-Bis-(2,9-dicyclohexyl-10-phenanthryl)- 4,5-dihydroimidazolium chloride 8 (H2ICP·HCl) with Pd(OAc)2 and KF·18-c-6 in THF at room temperature gave Suzuki-Miyaura coupling of aryl and vinyl chorides, including unactivated and di-ortho substituted substrates in high yields. Hindered tri- and tetra-ortho substituted products were also efficiently produced. Benzyl chloride was also found to be a useful coupling partner and trimethylboroxine was used to give methylated products. The effect of ligand, base, temperature, solvent, and reaction time are reported along with various substrates including halides and triflates.
- Song, Chun,Ma, Yudao,Chai, Qiang,Ma, Chanqin,Jiang, Wei,Andrus, Merritt B.
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p. 7438 - 7446
(2007/10/03)
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