- Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction
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A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.
- Chen, Yuan,Fang, Siqiang,Pan, Jianke,Ren, Xiaoyu,Tan, Jian-Ping,Wang, Tianli,Zhang, Hongkui
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supporting information
p. 14921 - 14930
(2021/05/10)
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- Ruthenium-catalyzed coupling of α-carbonyl phosphoniums with sulfoxonium ylidesviaC-H activation/Wittig reaction sequences
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A Ru(ii)-catalyzed coupling of various α-carbonyl phosphoniums with sulfoxonium ylides has been realized for the facile synthesis of 1-naphthols in good to excellent yields. This oxidant-free transformation proceeds through Ru-catalyzed C-H activation of phosphoniums, Ru-carbene insertion, and intramolecular Wittig reaction processes.
- Chen, Tian,Ding, Zhiqiang,Guan, Yuqiu,Zhang, Ruike,Yao, Jinzhong,Chen, Zhangpei
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supporting information
p. 2665 - 2668
(2021/03/16)
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- Cu(II)-Catalyzed 6π-Photocyclization of Non-6πSubstrates
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This research successfully achieved a Cu(II)-catalyzed 6π-photocyclization of non-6πsubstrates. The photoenolization converts ortho-alkylphenyl alkynl ketones into a triene-type intermediate which undergoes the subsequent 6π-photocyclization to give napht
- Zhang, Yanbin,Jin, Ruiwen,Kang, Wenjie,Guo, Hao
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p. 5502 - 5505
(2020/07/08)
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- Chemo- and Regioselective Catalyst-Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1-Indanones and 1-Naphthols
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A catalyst-controlled intramolecular carbocyclization of 2-alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1-indanones are formed through 5-exo-dig carbocyclizations with exclusive chemo-, regio- and stereoselectivity. When catalyzed by copper(I), 1-naphthols are obtained through 6-endo-dig carbocyclizations with exclusive chemo- and regioselectivity.
- Song, Liangliang,Tian, Guilong,Van der Eycken, Erik V.
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supporting information
p. 7645 - 7648
(2019/05/21)
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- AMINE-SUBSTITUTED NAPHTHALENE DERIVATIVES AND ORGANIC LIGHT EMITTING DIODES INCLUDING THE SAME
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Disclosed are amine-substituted naphthalene derivatives and organic light emitting diodes including the same. In the organic light emitting diodes, at least one of the amine-substituted naphthalene derivatives is employed in a hole auxiliary layer interpo
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Paragraph 0066-0067
(2019/05/18)
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- Anthracene derivatives and organic light emitting devices comprising the same
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An anthracene derivative represented by Formula 1 is disclosed. An organic light-emitting device including an anode, a cathode, and an organic layer between the anode and the cathode, where the organic layer includes at least one anthracene derivative represented by Formula 1, is also disclosed. A method of manufacturing the organic light-emitting device is also disclosed.
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Page/Page column 60
(2019/09/02)
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- Reaction of arynes with trifluoroacetylated β-diketones: Novel formation of isocoumarins and phenanthrenes
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Polysubstituted isocoumarins were synthesized by the reaction of substituted 2-(trimethylsilyl)aryl triflates with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded through carbon-carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β-diketones to afford phenanthrenes and 1,2-diarylethanones. Although reaction of 2-(trimethylsilyl)phenyl triflate with 1,1,1-trifluoro-4′-methylbenzoylacetone in the presence of CsF gave 3-(4′-methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9-(4-methylbenzoyl)-10-trifluoromethylphenanthrene in 35% yield.
- Okuma, Kentaro,Tanabe, Yukiko,Fukami, Takuto,Ishibashi, Yuto
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- aromatic compound having fused cyclic substituent in aromatic ring and organic light-emitting diode including the same
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The present invention relates to a compound having a cyclic substituent fused with a cyclic ring and an organic light emitting diode including the same, and more particularly, to a compound for an organic light emitting diode represented by chemical formula A and an organic light emitting diode including the same. In chemical formula A, X is a substituent having structural formula X, Y is a substituent of structural formula Y1, n is an integer from 1 to 4, and structural formulas X and Y1 are the same as described in detailed description of the present invention.
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Paragraph 0345; 0348; 0349
(2019/01/06)
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- ORGANIC LIGHT-EMITTING DIODE WITH HIGH EFFICIENCY AND LONG LIFETIME
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Disclosed herein is an organic light-emitting diode, comprising: an organic light-emitting diode, comprising: a first electrode; a second electrode facing the first electrode; a light-emitting layer intercalated between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one of the amine compounds represented by Chemical Formula A or B, and at least one of the anthracene compounds represented by Chemical Formula C.
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Paragraph 0151; 0152
(2017/01/31)
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- An electroluminescent compound and an electroluminescent device comprising the same
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The present invention relates to an organic light emitting compound applied to an organic electroluminescent device. The organic light emitting compound is represented by [chemical formula 1] and has a substituent represented by [structural formula 1] or [structural formula 2]. When the organic light emitting compound is applied as a host compound or a dopant compound in a light emitting layer, the organic electroluminescent device with excellent light emitting properties such as driving voltage, brightness, and durability can be provided. [chemical formula 1] [structural formula 1] [structural formula 2]COPYRIGHT KIPO 2016
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Paragraph 0122; 0132-0134; 0159-0161
(2016/10/08)
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- NOVEL COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
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Disclosed are a compound for an organic electroluminescent device, and an organic electroluminescent device comprising the same. Accordingly, provided is a compound for an organic electroluminescent device, which can be used as a host and a hole transport material having excellent electrical stability and hole transporting capability and improving light emitting efficiency of a phosphorescent material by having a high triplet energy. An organic electroluminescent device is also provided. The compound for an organic electroluminescent device is represented by structural formula 1.COPYRIGHT KIPO 2016
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Paragraph 0115; 0304-0307
(2016/10/27)
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- An electroluminescent compound and an electroluminescent device comprising the same
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The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1. When adopting the organic light emitting compound as a dopant compound or a hole transfer compound in a luminous layer, the organic electroluminescent device has excellent light emitting characteristics such as operating voltage, brightness, long lifespan, and the like.COPYRIGHT KIPO 2016
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Paragraph 0260; 0272; 0341; 0345-0347
(2016/10/09)
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- An electroluminescent compound and an electroluminescent device comprising the same
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In the present invention refers to light emitting layer dopant compounds arylamine of the existing method, such as low-voltage included in the drive and, the water life characteristics which can be the substrate by including compounds, liquid indicates or
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Paragraph 0123-0126
(2017/01/31)
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- An electroluminescent compound and an electroluminescent device comprising the same
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The present invention relates to an organic light emitting compound adopted to an organic electroluminescent device. The organic light emitting compound is represented by chemical formula 1. In the case of adopting the same as a dopant compound in a lumin
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Paragraph 0126; 0162; 0163; 0164; 0165
(2016/10/10)
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- Facile synthesis of 1-naphthols through a copper-catalyzed arylation of methyl ketones with o-bromoacetophenones
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The coupling reactions of simple methyl ketones with o-bromoacetophenones and subsquential cyclization reactions were realized to produce a range of 1-naphthols. These cascade reactions were initiated by a rare Cu-catalyzed arylation reaction of methyl ketones with aromatic bromides.
- Lou, Zhen-Bang,Pang, Xin-Long,Chen, Chao,Wen, Li-Rong,Li, Ming
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supporting information
p. 1231 - 1235
(2015/12/30)
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- Enantioselective Synthesis of 4,4′-Biaryl-BINOLs from Arynes and β-Diketones
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The reaction of 2-(trimethylsilyl)phenyl triflate with aroylacetones in the presence of CsF gave the corresponding 4-aryl-2-naphthols. Substituted triflates also reacted with aroylacetones to afford 4-aryl-2-naphthols regioselectively. The enantioselectiv
- Okuma, Kentaro,Horigami, Kenta,Nagahora, Noriyoshi,Shioji, Kosei
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p. 2937 - 2944
(2015/09/28)
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- aromatic compound having fused cyclic substituent in aromatic ring and organic light-emitting diode including the same
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The present invention refers to to the aromatic ring-fused ring withdrawing substituent and a compound having an same relates to organic light emitting device including, more specifically a represented by [formula A] an alkali-soluble polymer resin compound for an organic light-emitting device including organic light emitting device is characterized in that the. [Formula A] In said [formula A], X has a dementia drug; and shows strong X having substituted group, Y has a dementia drug; and shows strong formula selected from the group consisting Y1 to Y5 having one of substituted group, the n being integers, of 4 to 1, the Y5 formula to Y1 formula and X formula detailed description of the invention is described. (by machine translation)
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Paragraph 0359; 0360
(2016/10/10)
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- Concise synthesis of 1-naphthols under mild conditions through a copper-catalyzed arylation of methyl ketones
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A concise synthesis of 1-naphthols via cyclization of o-iodoacetophenones and methyl ketones has been realized under very mild conditions. The cyclization process is initiated by a rare coppercatalyzed arylation of simple methyl ketones with ortho-iodoacetophenones.
- Lou, Zhenbang,Zhang, Shu,Chen, Chao,Pang, Xinlong,Li, Ming,Wen, Lirong
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p. 153 - 159
(2014/03/21)
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- Tandem carbon-carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: Novel formation of 4,4′-disubstituted 1,1′-binaphthols
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An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon-carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoyla
- Okuma, Kentaro,Itoyama, Ryoichi,Sou, Ayumi,Nagahora, Noriyoshi,Shioj, Kosei
-
supporting information
p. 11145 - 11147
(2013/01/15)
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- Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: Arene functionalization with activating group recycling
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A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process.
- Hooper, Joel F.,Chaplin, Adrian B.,Gonzalez-Rodriguez, Carlos,Thompson, Amber L.,Weller, Andrew S.,Willis, Michael C.
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supporting information; experimental part
p. 2906 - 2909
(2012/03/27)
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- A succinct synthesis of the vaulted biaryl ligand vanol via a dienone-phenol rearrangement
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Vanol is a member of the vaulted biaryl family of ligands and it has been proven to be very effective in a number of asymmetric catalytic reactions. The previous synthesis of vanol, while effective, is limited by the cost of reagents involved. The present work evaluates three different approaches to the synthesis of 3-phenyl-1-naphthol, a key intermediate in the synthesis of vanol. The first approach has its key step as the Michael addition of a benzyl Grignard to methyl cinnamate. In the second approach the key step is the first step, a Reformatsky reaction of ethyl bromoacetate and deoxybenzoin. The final and most-efficient approach involves a dienone-phenol rearrangement of a 4-aryl-1-tetralenone generated in-situ from the reaction of 4-chloro-1-naphthol with AlCl3 and benzene, and preliminary results are reported on the extension of this method to substituted vanol derivatives.
- Ding, Zhensheng,Xue, Song,Wulff, William D.
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scheme or table
p. 2130 - 2146
(2011/10/18)
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- 1-(1-Naphthyl)piperazine as a novel template for 5-HT6 serotonin receptor ligands
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4-Sulfonyl analogs of 1-(1-naphthyl)piperazine bind at human 5-HT 6 receptors and represent a novel class of human 5-HT6 receptor ligands.
- Lee, Mase,Rangisetty, Jagadeesh B.,Pullagurla, Manik R.,Dukat, Malgorzata,Setola, Vince,Roth, Bryan L.,Glennon, Richard A.
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p. 1707 - 1711
(2007/10/03)
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- Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2′-binaphthol and a vaulted 3,3′-biphenanthrol (VAPOL)
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Two methods for the synthesis of vaulted biaryls were developed involving the reactions of carbene complexes with alkynes and the [2 + 2] cycloaddition of ketenes. The final step in the synthesis of 3,3′-diphenyl-[2,2′-binaphthalene]-1,1′-diol (39) and 2,2′-diphenyl-[3,3′-biphenanthrene]-4,4′-diol (47) (VAPOL) was phenol coupling of the 3-phenyl-1-naphthol (14) and the 2-phenyl-4-phenanthrol (28), respectively. The naphthol 14 could be prepared from the thermolysis of phenylacetyl chloride in the presence of phenylacetylene or from the benzannulation of the pentacarbonyl(phenylmethoxymethylene)chromium(0) (15) with phenylacetylene which upon an acetylative workup gives O-acetyl-4-methoxy-2-phenyl-1-naphthol (16). The reductive cleavage of the acetoxy group in 16 was unexpectedly affected by aluminum chloride and ethanethiol which were used to cleave the methyl ether. In a similar manner, the phenanthrol 28 could either be prepared from the 1-naphthylacetyl chloride (30) or pentacarbonyl-(1-naphthylmethoxymethylene)chromium(0) (21). A new procedure for the preparation of carbene complexes was developed utilizing dimethyl sulfate as methylating agent. Unlike the benzannulation of the phenyl complex 15, the benzannulation of the naphthylcarbene complex 21 with phenylacetylene gave a side product which resulted from the incorporation of 2 equiv of the alkyne. This side product could be minimized by the proper control of the concentration of the alkyne. The phenol coupling of the 3-phenyl-1-naphthol with ferric chloride gave 2,2′-diphenyl-[2,2′-binaphthalene]-4,4′-diol (38) and with air as oxidant gave the of 3,3′-diphenyl-[2,2′-binaphthalene]-1,1′-diol (39). Oxidative coupling of the 2-phenyl-4-phenanthrol (28) with air gave 2,2′-diphenyl-[3,3′-biphenanthrene]-4,4′-diol (47) (VAPOL), but the same coupling with 2-tert-butyl-4-phenanthrol (34) failed. The 2,2′-binaphthol 39 was resolved via its cyclic diester with phosphoric acid by salt formation with (-)-brucine, and the 3,3′-biphenanthrol 47 was resolved via its cyclic deiester with phosphoric acid (49) by salt formation with (-)-cinchonidine. The configuration of (-)-39 was shown to be S from an X-ray analysis of the brucine salt, and the configuration of (+)-47 was shown to be S from an X-ray analysis the amide (S,S)-54 derived from 49 and (S)-α-methylbenzylamine.
- Bao, Jianming,Wulff, William D.,Dominy, James B.,Fumo, Michael J.,Grant, Eugene B.,Rob, Alexander C.,Whitcomb, Mark C.,Yeung, Siu-Man,Ostrander, Robert L.,Rheingold, Arnold L.
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p. 3392 - 3405
(2007/10/03)
-
- REACTION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS. XIII. REACTION OF DERIVATIVES OF 2-NAPHTHOL WITH BENZENE. REGIOSELECTIVITY AND REACTION MECHANISM
-
1-Methyl and 1-phenyl-2-naphthols react with benzene in the presence of aluminum chloride with the formation of 1-methyl-4-phenyl- and 1,4-diphenyl-2-tetralones respectively. 1,3-Naphthalenediol and its dimethyl ether enter into an analogous reaction in the presence of aluminum chloride or in the HF-SbF5 system with the formation of 3-phenyl-1-naphthol and its methyl ether respectively.It was concluded that the regioselectivity and other features of the condensations are due to the reactivity of the key intermediates of the reaction, i.e., the diprotonated forms of the 2-naphthols (dications) or, for the analogs in the presence of aluminum halides, the mono-C-protonated complexes of the tautomeric keto forms of naphthols with the aluminum halides.The latter agrees with the results from MNDO quantum-chemical calculations for the dications.
- Koltunov, K. Yu.,Repinskaya, I. B.,Shakirov, M. M.,Shchegoleva, L. N.
-
-
- Acyl Cyanides as Carbonyl Heterodienophiles
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Acyl cyanides have been shown to behave as carbonyl dienophiles in reactions with electron-rich o-quinodimethanes.This represents the first observation of an acyl cyanide carbonyl group reacting in such a manner.
- Connors, Richard,Durst, Tony
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p. 7277 - 7280
(2007/10/02)
-
- The Chemistry of Phthalide-3-carboxylic Acid. III. Decarboxylation of Salts in the Presence of α,β-Unsaturated Ketones
-
Potassium phthalide-3-carboxylate (3-oxo-1,3-dihydroisobenzofuran-1-carboxylate) decarboxylates readily in dimethyl sulfoxide at 145 deg C, and the intermediate phthalidyl anion is efficiently trapped by α,β-unsaturated ketones.The major 1,4-addition product is accompanied by smaller amounts of an isomeric product formed by subsequent cyclization and rearrangement, and sometimes traces of a 1:2 1,4-addition product.The caesium salt gives slightly more cyclized product, and the lithium salt undergoes very slow decarboxylation.The synthetic usefulness of the salt decarboxylation is compared with that of the free acid.
- Janowski, Wit K.,Prager, Rolf H.
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p. 921 - 929
(2007/10/02)
-
- CONDENSATION OF PHENOLS AND THEIR DERIVATIVES WITH AROMATIC COMPOUNDS IN THE PRESENCE OF ACIDIC AGENTS. V. REACTIONS OF CHLORINE-SUBSTITUTED NAPHTHOLS WITH BENZENE
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Substitution of the chlorine at position 1 by a phenyl residue occurs readily in the reaction of 1-chloro- and 1,4-dichloro-2-naphthols with benzene in the presence of aluminum chloride and hydrogen chloride. 4-Chloro-2-naphthol reacts with considerably great difficulty, giving a small yield of 4-phenyl-2-naphthol.The possibility of using a mixture of 4- and 2-chloro-1-naphthols for the production of 3-phenyl-1-naphthol was demonstrated.The possible reaction paths are discussed.
- Repinskaya, I. B.,Savel'ev, V. A.,Makarova, Z. S.,Koptyug, V. A.
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p. 1463 - 1466
(2007/10/02)
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