- A 1,2-Addition Pathway for C(sp2)?H Activation at a Dinickel Imide
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A dinickel imido complex was synthesized using a redox-active naphthyridine-diimine supporting ligand. Upon coordination of an external ligand, the Ni2 core was disrupted, triggering an aromatic C?H activation reaction to generate a Ni2(μ-NHAr)(Ar) species. This intermediate is capable of liberating free carbazole and phenanthridine products upon heating or treatment with excess tBuNC. Collectively, these studies establish a kinetically facile 1,2-addition mechanism for C(sp2)?H activation, taking advantage of cooperative reactivity between two Ni centers.
- Powers, Ian G.,Kiattisewee, Cholpisit,Mullane, Kimberly C.,Schelter, Eric J.,Uyeda, Christopher
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- Catalytic C(sp2)?H amination reactions using dinickel imides
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C?H amination reactions are valuable transformations for the construction of C?N bonds. Due to their relatively high bond dissociation energies, C(sp2)?H bonds are generally not susceptible toward direct nitrene insertion, necessitating alternative mechanisms for C?H activation. Here, we report that cationic dinuclear (NDI)Ni2 (NDI = naphthyridine?diimine) complexes catalyze intramolecular nitrene insertions into aryl and vinyl C(sp2)? H bonds. Mechanistic studies suggest that a bridging imido ligand supported at a Ni2 site induces C?H activation by a 1,2-addition pathway to generate an azametallacyclic intermediate. This organometallic mechanism contrasts with the electrocyclization/1,2-shift mechanism proposed for analogous transformations using Rh2 catalysts. The implications of these mechanistic differences for the stereoselectivity and chemoselectivity of C?H amination are described.
- Andjaba, John M.,Powers, Ian G.,Uyeda, Christopher,Zeller, Matthias
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- Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation
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A three-component reaction of indoles, α-bromoacetaldehyde acetals, and ketones was developed by using bismuth(III) triflate as the catalyst to realize a straightforward approach for synthesizing carbazole derivatives. The reaction was established mechanistically through the autotandem catalysis of Bi(OTf)3 in the following two steps: (i) Friedel-Crafts-type alkylation of indole with α-bromoacetaldehyde acetal, which produced a tryptaldehyde-type intermediate and (ii) [4 + 2] annulation of this intermediate with the ketone component.
- Gu, Yanlong,Huang, Wenbo,Chen, Shaomin,Wang, Xin
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- Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones
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Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearo
- Liddon, John T. R.,James, Michael J.,Clarke, Aimee K.,O'Brien, Peter,Taylor, Richard J. K.,Unsworth, William P.
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- Temporary (P=O) directing group enabled carbazoleorthoarylationviapalladium catalysis
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A palladium-catalyzed, temporary P(O) directing group assisted C-H bond arylation of carbazoles was achieved. The release of the directing group occurs spontaneously in the reaction and the mechanistic studies indicate that acid is essential for N-P bond cleavage.
- Qi, Zhi-Chao,Lou, Qin-Xin,Niu, Yuan,Yang, Shang-Dong
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supporting information
p. 2021 - 2024
(2021/03/01)
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- A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present disclosure relates to a plurality of host materials comprising a first host material comprising a compound represented by formula 1, and a second host material comprising a compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds as host materials, it is possible to provide an organic electroluminescent device having lower driving voltage, higher luminous efficiency, higher power efficiency, and/or superior lifespan characteristics compared to conventional organic electroluminescent devices.
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Paragraph 0216-0219
(2021/05/08)
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- Plurality of host materials and organic electroluminescent device comprising the same
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The present disclosure relates to a plurality of host materials comprising a first host material comprising a compound represented by formula 1, and a second host material comprising a compound represented by formula 2, and an organic electroluminescent d
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Paragraph 0229-0232
(2021/04/29)
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- PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present disclosure relates to a plurality of host materials comprising a first host material comprising a compound represented by formula 1, and a second host material comprising a compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds as host materials, it is possible to provide an organic electroluminescent device having higher luminous efficiency, higher power efficiency, and/or better lifetime properties, compared to conventional organic electroluminescent devices.
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Paragraph 0076-0078
(2021/06/11)
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- Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
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The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Specifically, disclosed are a compound for an organic optoelectronic device represented by a combination of Chemical Formula 1 and Chemical Formula 2, and a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device comprising the same. Details of the chemical formula 1 and the chemical formula 2 are described in the specification.
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Paragraph 0208-0212; 0323-0327
(2021/10/30)
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- HETEROCYCLIC COMPOUND, COMPOSITION INCLUDING THE SAME, AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE HETEROCYCLIC COMPOUND
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A heterocyclic compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.
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Paragraph 0300-0302
(2019/07/23)
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- A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes
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A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.
- Banerjee, Ankush,Maji, Modhu Sudan
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supporting information
p. 11521 - 11527
(2019/08/16)
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- TfOH catalyzed synthesis of 1-substituted tetrahydrocarbazoles
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Synthesis of 1-substituted tetrahydrocarbazole is accomplished by TfOH catalyzed reaction of 3-substituted indoles tethered with secondary and tertiary alcohols. The reaction was generalized for a variety of substrates and was extended to the synthesis of
- Nanda, Laxmi Narayan,Rangari, Vipin Ashok
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p. 3194 - 3197
(2018/07/21)
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- ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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The present invention relates to an organic electroluminescent device having improved properties such as light emitting efficiency, driving voltage, lifespan, etc. by including a novel compound with excellent heat resistance, a hole transporting function, a light emitting function, etc. in one or more organic matter layers. The organic electroluminescent device of the present invention includes (i) a positive electrode, (ii) a negative electrode, and (iii) one or more layers of organic matter layers interposed between the positive and negative electrodes.COPYRIGHT KIPO 2017
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Paragraph 0217; 0340-0343
(2017/09/21)
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- A carbazole compound and its preparation method, the organic electroluminescent device (by machine translation)
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This invention has offered a kind of carbazole compound, the carbazole compound of formula (1) structure. Compared with the prior art, the present invention provides the carbazole compound is introduced in the carbazole compound is connected with the ethe
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Paragraph 0119; 0120; 0121; 0122
(2016/10/10)
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- Direct ortho arylation of 9-(pyridin-2-yl)-9 h-carbazoles bearing a removable directing group via palladium(II)-catalyzed C-H bond activation
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A one-pot synthesis of ortho-arylated 9-(pyridin-2-yl)-9H-carbazoles via C-H bond activation is presented. Silver nitrate and tert-butyl alcohol were found to be the best oxidant and solvent for the process, respectively. The product yields are from modest to excellent, and the reaction showed sufficient functional group tolerance. p-Benzoquinone served as an important ligand for the transmetalation and reductive elimination steps in the catalytic process. The key intermediate of the reaction, a 9-(pyridin-2-yl)-9H-carbazole palladacycle, was isolated, and its structure was unequivocally confirmed by X-ray crystallography. No kinetic isotope effect (kH/kD = 1.00 ± 0.17) for the C-H bond activation step was observed. In addition, a Hammett experiment gave a negative ρ value,-2.16 ± 0.02. The directing group, pyridinyl, was demonstrated to be a removable functional group. Finally, a rational catalytic mechanism is presented on the basis of all experimental evidence.
- Chu, Jean-Ho,Wu, Chung-Chiu,Chang, Deng-Hsiang,Lee, Ya-Ming,Wu, Ming-Jung
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p. 272 - 282
(2013/02/25)
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- Synthesis of carbazoles by intramolecular arylation of diarylamide anions
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(Chemical Equation Presented) The synthesis of a series of substituted 9H-carbazoles by the photostimulated SRN1 substitution reaction with diarylamines as starting substrate was performed. The diarylamines were obtained by two approaches, the Pd-catalyzed reactions (Buchwald-Hartwig) or Cu-catalyzed reactions of 2-haloanilines with aryl halides, or 2-bromoiodobenzene with anilines, with moderate to very good isolated yields (45-89%). Through an intramolecular C-C bond formation of diarylamines by the SRN1 mechanism, carbazoles were achieved. These reactions proceeded synthetically in very good to excellent yields (81-99%) in liquid ammonia and DMSO. The reaction of N-(2-bromophenyl)-2-phenylbenzenamine gave 1-phenyl-9H-carbazole (38%) and the isomer 9H-tribenz[b,d,f]azepine (58%). By using this methodology, 9Hcarbazoles, substituted 9H-carbazoles, benzocarbazoles, and even 3,3′-bi(9H-carbazole) were obtained by a double SRN1 reaction with benzidine.
- Buden, Maria E.,Vaillard, Victoria A.,Martin, Sandra E.,Rossi, Roberto A.
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experimental part
p. 4490 - 4498
(2009/09/26)
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- Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. II. N-Phenylation of Diarylamines
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The condensations of 1,4-cyclohexanedione with several diphenylamines were investigated in order to determine the limit of the utility of this reaction for the N-phenylation of aromatic secondary amines. 4-Methoxy-, 4,4'-dimethyl-, and 4,4'-dibromodiphenylamines produced their N-phenylated compounds in fairly good yields, but 4-hydroxy-, 3-methoxy-, and 4,4'-bis(dimethylamino)diphenylamines produced poor yields.Nitro-substituted diphenylamines gave N-phenyl derivatives in low yields along with N-4-hydroxyphenyl derivatives.N,N'-Diphenyl-p-phenylenediamine and N,N'-diphenylbenzidine gave correspondig tetra-N-phenyl diamines in good yields.The condensation of N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-2-pyridylamine, phenothiazine, and carbazole with 1,4-cyclohexanedione were also examined.
- Haga, Kazuo,Iwaya, Katsumasa,Kaneko, Ryohei
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p. 803 - 808
(2007/10/02)
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- A TRIFLUOROMETHANESULFONIC ACID-CATALYZED REACTION OF ARYLHYDRAZINES WITH BENZENE
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Arylhydrazines reacted with benzene in the presence of trifluoromethanesulfonic acid (TFSA) to give aminobiphenyls.This is a general method for the synthesis of aminobiphenyls.
- Ohta, Toshiharu,Miyake, Shinji,Shudo, Koichi
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p. 5811 - 5814
(2007/10/02)
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