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TRIPHENYLENE-BASED COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME

The present invention relates to a triphenylene-based compound represented by the following Formula 1 and an organic electroluminescent device including the same, and the compound of the present invention has excellent hole injection and/or transporting ability, electron transporting ability, and/or light emitting ability, and particularly, green and red light emitting ability, and thus in an organic electroluminescent device containing the same as a light emitting host material, characteristics such as luminous efficiency, luminance, thermal stability, driving voltage, service life and the like may be improved. In the formula, each of A, L, X and R1 to R19 is the same as those as defined in Detailed Description.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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2-(IMIDAZOLYLAMINO)-PYRIDINE DERIVATIVES AND THEIR USE AS JAK KINASE INHIBITORS

The present invention relates to compounds of Formula (I): or a pharmaceutically acceptable salt thereof, wherein Ring A is 5- or 6-membered heteroaryl, wherein said 5- or 6-membered heteroaryl is optionally substituted on carbon with one or more R6 , and wherein if said 5- or 6- membcred heteroaryl contains an -NH- moiety, that -NH- moiety is optionally substituted with R6 ; D is selected from N and C-R3 ; E is selected from N and C-R4 , wherein at least one of D and E is carbon; X is selected from -NH-, -O-, and -S-; and to their pharmaceutical compositions, methods of use, and methods for their preparation. These compounds provide a treatment for myeloproliferative disorders and cancer

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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A general synthesis of alpha-trifluoromethylstyrenes through palladium-catalyzed cross-couplings with 1,1,1-trifluoroacetone tosylhydrazone

1,1,1-Trifluoroacetone tosylhydrazone is presented as a very convenient substrate for the palladium-catalyzed cross-coupling with aryl halides. Under the proper reaction conditions, 3,3,3-trifluoromethylstyrenes – very valuable trifluoromethylated synthetic intermediates – are obtained with high yields. The reaction features a very wide scope, as the presence of most functional groups is tolerated. Moreover, the reaction has been extended to substituted trifluoromethylstyrenes by employing substituted tosylhydrazones derived from other trifluoromethyl ketones.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes

Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins constitute one of the most efficient methods to access them. In this context, oxy- and aminoalkynylation are especially important reactions, because of the numerous transformations possible with the triple bond of acetylenes, yet these methods have been limited to the use of silyl protected acetylenes. Herein, we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes, which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally, a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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In situ synthesis of alkenyl tetrazines for highly fluorogenic bioorthogonal live-cell imaging probes

In spite of the wide application potential of 1,2,4,5-tetrazines, particularly in live-cell and in vivo imaging, a major limitation has been the lack of practical synthetic methods. Here we report the in situ synthesis of (E)-3-substituted 6-alkenyl-1,2,4,5-tetrazine derivatives through an elimination-Heck cascade reaction. By using this strategy, we provide 24 examples of pi-conjugated tetrazine derivatives that can be conveniently prepared from tetrazine building blocks and related halides. These include tetrazine analogs of biological small molecules, highly conjugated buta-1,3-diene-substituted tetrazines, and a diverse array of fluorescent probes suitable for live-cell imaging. These highly conjugated probes show very strong fluorescence turn-on (up to 400-fold) when reacted with dienophiles such as cyclopropenes and trans-cyclooctenes, and we demonstrate their application for live-cell imaging. This work provides an efficient and practical synthetic methodology for tetrazine derivatives and will facilitate the application of conjugated tetrazines, particularly as fluorogenic probes for live-cell imaging. Stitching probes together: The in situ synthesis of (E)-3-substituted 6-alkenyl-1,2,4,5-tetrazine derivatives through an elimination-Heck cascade reaction is reported. 24 examples of pi-conjugated tetrazine derivatives are provided, including conjugated fluorescent probes that show drastic fluorescent turn-on when reacted with dienophiles. Their suitability for live-cell imaging is demonstrated. TCO=trans-cyclooctene.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Catalytic carbonylation of renewable furfural derived 5-bromofurfural to 5-formyl-2-furancarboxylic acid in oil/aqueous bi-phase system

Utilizing sustainable biomass to partly replace the fossil feedstock as the carbon source of chemical industry has been well acknowledged because of the scarcity of the fossil resources. This work introduced a novel route for the synthesis of 5-formyl-2-furancarboxylic acid (FFA) from renewable furfural derived 5-bromofurfural, which achieves the transformation of furfural based platform molecule to the products having multifunctional groups, thus opens up its potential market in polymeric applications. Under the optimized conditions, this new catalysis provided up to 99% yield of FFA through oil/aqueous bi-phasic carbonylation. Remarkably, the FFA product could be feasibly separated from the remaining substrate and catalyst because of its aqueous solubility in the biphasic system, giving 95% isolated yield in gram scale synthesis. Currently, FFA is an unstable intermediate in hydroxymethylfurfural (HMF) oxidations; in viewing of that furfural is industrially produced from bulky agroforestrial byproducts, this furfural based route to FFA through catalytic carbonylation has offered an opportunity for its production in large scale.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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eta5-cyclopentadienyl-eta3-1- phenylallylpalladium, an unusually effective catalyst precursor for copper-free and copper-assisted sonogashira cross-coupling reactions catalyzed by bis-phosphine palladium(0) compounds: The role of bis-acetylide intermediates in the reduction of a palladium(II) catalyst precursor to a palladium(0) catalyst

It has been demonstrated previously that Pd(eta3-1-PhC 3H4)(eta5-C5H5) (I) reacts with a number of phosphines L to form two-coordinate, zerovalent species of the type PdL2, known to be effective cross-coupling catalysts for Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions. Formation of PdL 2 from I is generally rapid and near quantitative, and I has therefore been found to be much more effective than more commonly utilized precursors such as Pd(PPh3)4, Pd2(dba) 3, and Pd(OAc)2, which do not efficiently generate PdL2. This advantage is expected to apply as well to Sonogashira cross-coupling reactions, which are also believed to be catalyzed by species of the type PdL2, and it is shown that the I/2PPh3 catalyst system is much more active for the representative, conventional coupling reaction of bromobenzene with phenyl acetylene to form diphenylacetylene than are conventional catalyst systems based on Pd(PPh3)4, trans-PdCl2(PPh3)2, Pd2(dba) 3/PPh3, and Pd(OAc)2/PPh3, the latter two activated with appropriate amounts of PPh3. Complementary studies involving the use of PBut3 with I, which generates an extremely active catalyst system, and the involvement of the cocatalyst CuI are also described, as is the catalytic competence of trans-Pd(C 2Ph)2(PPh3)2, long considered to be an intermediate in the activation of trans-PdCl2(PPh 3)2 but not heretofore, to our knowledge, shown to be viable.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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5-Bromo-norborn-2-en-7-one derivatives as a carbon monoxide source for palladium catalyzed carbonylation reactions

Norbornenone (5b), obtained from the reaction of 2,5-dimethyl-3,4-diphenylcyclopentadienone dimer (3) with bromomaleic anhydride (4b), provides an excellent base-triggered source of carbon monoxide for palladium-catalysed carbonylation reactions. Aminocarbonylation, ketoamide synthesis, and Suzuki-Miyaura reactions of aryl iodides carried out in a two-chamber reaction vessel gave good to excellent yields of carbonylated products.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Process for preparing mono-carboxy-functionalized dialkylphosphinic acids, esters and salts by means of alkylene oxides and use thereof

A process for preparing mono-carboxy-functionalized dialkylphosphinic acids, dialkylphosphinic esters and dialkylphosphinic salts by means of alkylene oxides, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to form an alkylphosphonous acid, its salt or ester (II), b) the resultant alkylphosphonous acid, its salt or ester (II) is reacted with alkylene oxides of the formula (V) in the presence of a catalyst B, to give a mono-functionalized dialkylphosphinic acid derivative (VI), and c) the resultant mono-functionalized dialkylphosphinic acid derivative (VI) is reacted in the presence of a catalyst C to give the mono-carboxy-functionalized dialkylphosphinic acid derivative (III), and the catalysts A and C are transition metals and/or transition-metal compounds and/or catalyst systems which are composed of a transition metal and/or a transition-metal compound and at least one ligand, and the catalyst B is a Lewis acid.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Organometallic Gold Catalysis in Combination with Enzyme, Organo-, or Transition-Metal Catalysis

This chapter is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of organobismuth compounds and their use in organic synthesis. Organobismuth compounds are organometallic species that contain a carbon-bismuth bond. These species have been used as catalysts and reagents in various reactions that lead to the formation of carbon-carbon, carbon-nitrogen, carbon-oxygen, carbon-sulfur, and carbon-selenium bonds.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method