- Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
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In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
- Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup
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p. 10966 - 10972
(2020/09/23)
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- Preparation method of 4-phenoxy phenylboronic acid
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The invention discloses a preparation method of 4-phenoxy phenylboronic acid, which belongs to the technical field of organic boric acid chemistry. The preparation method comprises the following steps: starting from diphenyl ether, reacting with NBS to generate 4,4'-dibromo diphenyl ether, reacting with borate and butyl lithium by a one-pot method, and hydrolyzing to obtain 4-phenoxy phenylboronicacid. According to the method, dibromides which are easy to purify are generated during bromination, monosubstituted products are generated by controlling the using amount of a lithiation reagent andthe boric acid ester during lithiation, the method is verified on the scale of 100 kg, and the method has the prospect of industrial methods.
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Page/Page column 4-6
(2020/05/14)
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- Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis
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Flow chemistry processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technology was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production. Some of the key benefits of flow flash chemistry were utilized, both to avoid side reactions and to enable dianion chemistry that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development.
- Usutani, Hirotsugu,Cork, David G.
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p. 741 - 746
(2018/06/11)
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- Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates
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Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.
- Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong
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p. 4253 - 4257
(2018/09/18)
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- Anthracene compound, preparing method of anthracene compound and organic light-emitting device
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The invention provides an anthracene compound. The anthracene compound has a structure in the formula (I), wherein Q is the C1-60 alkyl group or the C6-60 aryl group or the C5-60 condensed ring group or the C5-60 heterocyclic group; Ar is the C6-60 aryl group or the C5-60 condensed ring group or the C5-60 heterocyclic group; and Ar1 is H, the C1-60 alkyl group, the C1-60 alkoxy group, the C1-60 ether group, the C6-60 aryl group, the C6-60 condensed ring group, the C6-60 heterocyclic group and the C6-60 arylamine group. Compared with the prior art, the anthracene compound is connected with an aromatic compound through anthracene, and the Q, Ar and Ar1 groups are introduced, so that a device emits blue light after the organic compound is applied to the organic light-emitting device; and meanwhile, the means that the above groups are used for adjusting the light-emitting wavelength is adopted, the light-emitting efficiency of the organic light-emitting device is high, and the service life is long.
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Paragraph 0131; 0132-0136
(2017/05/02)
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- Platinum(II) cyclometallates featuring broad emission bands and their applications in color-tunable OLEDs and high color-rendering WOLEDs
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Two phosphorescent platinum(ii) cyclometallated complexes with phenoxy groups (1 and 2) have been developed. The modified organic ligands derived by combining the phenoxy moiety and 2-phenylpyridine conferred them with a more flexible structure, leading to superior intermolecular interaction properties of the resulting Pt(ii) metallophosphors. Because of the excimer formation induced by Pt(ii) complexes 1 and 2, the emission color can be tuned over a wide range from cyan to orange by simply increasing the concentration of the Pt(ii) metallophosphors. Inspired by their broad emission band, color tunability and outstanding electroluminescence (EL) performance, these two Pt(ii) phosphors complemented with blue fluorescent emitter 4,4′-bis(9-ethyl-3-carbazovinylene)-1,1′-biphenyl (BCzVBi) were employed in manufacturing high color-rendering white organic light-emitting devices (WOLEDs). In such simple two-emitter systems, 1-based WOLEDs exhibited reasonable EL performance with an external quantum efficiency (ηext) of 11.7%, luminance efficiency (ηL) of 29.1 cd A-1, power efficiency (ηp) of 16.9 lm W-1 and color rendering index (CRI) of 77, whereas 2-based WOLEDs demonstrated an ηext of 10%, ηL of 21.7 cd A-1, ηp of 10.7 lm W-1 and CRI of 88.
- Tan, Guiping,Chen, Shuming,Siu, Chi-Ho,Langlois, Adam,Qiu, Yongfu,Fan, Hongbo,Ho, Cheuk-Lam,Harvey, Pierre D.,Lo, Yih Hsing,Liu, Li,Wong, Wai-Yeung
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p. 6016 - 6026
(2016/07/06)
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- Compound containing anthracene and pyrene and preparing method and application thereof
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The invention provides a compound containing anthracene and pyrene and a preparing method and application thereof. The compound has a structure shown in formula I, wherein R1 and R3 are independently selected from substituted or unsubstituted C1-C60 alkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C10-C60 condensed ring groups or substituted or unsubstituted C5-C60 heterocyclic groups; R2 is selected from hydrogen, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C5-C60 heterocyclic groups, substituted or unsubstituted C10-C60 condensed ring groups or substituted or unsubstituted C5-C60 arylamine groups; n is 0 or 1. When current density is 20 mA/cm2, the current efficiency of the compound with the structure shown in formula I is as high as 8.9 cd/A, and service life is as long as 8500 h which is much longer than that of existing electroluminescent materials.
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Paragraph 0147-0153
(2017/02/24)
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- New organic electroluminescent material, preparation method and applications thereof
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The invention relates to a new organic electroluminescent material, a preparation method and applications thereof, and provides a new anthracene derivative, wherein an ether structure is introduced into an anthracene compound to link Y1, Ar1, Ar2 and R1 so as to improve the stereo skill of the compound, adjust the molecular weight of the ligand R1, carry out performance improving and skill improving according to ligand type performance, and provide other advantages. The device prepared by using the new anthracene derivative of the present invention has characteristics of high brightness, excellent heat resistance, long service life, high efficiency, and the like.
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Paragraph 0047; 0048; 0049; 0050
(2016/10/09)
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- Preparation method of 4-phenoxyphenylboronic acid
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The invention discloses a preparation method of 4-phenoxyphenylboronic acid, and relates to the technical field of organic synthesis. The preparation method comprises the steps that 4-bromodiphenyl ether is taken as a raw material to react with magnesium sheets to prepare a Grignard reagent by taking tetrahydrofuran as a solvent, the obtained Grignard reagent reacts with trimethyl borate, hydrochloric acid hydrolysis is conducted to prepare coarse 4-phenoxyphenylboronic acid, and then purifying is conducted to obtain the finished 4-phenoxyphenylboronic acid. According to the preparation method, the adopted raw materials are low in cost and easy to obtain, the reaction conditions are mild, aftertreatment operation is easy, the production cost is low, the yield is high, and the method is suitable for industrialized production.
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Paragraph 0018; 0019; 0022; 0023; 0026; 0027; 0029-0032
(2018/02/04)
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- Pyrazolopyrimidine derivative, preparation method, pharmaceutical composition and application
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The invention discloses a pyrazolopyrimidine derivative, a preparation method, a pharmaceutical composition and application. The invention provides the pyrazolopyrimidine derivative as shown in a formula I and stereoisomer or solvate or pharmaceutically acceptable salts or active metabolite or prodrug thereof. The pyrazolopyrimidine derivative as shown in the formula I has good inhibitory activity on Bruton's tyrosine kinase (Btk) and particularly has good in vitro and in vivo inhibitory activity on growth of tumor cells, and a good marketization prospect is achieved. Please see the formula I in the description.
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Paragraph 0147; 0148; 0149
(2017/07/19)
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- Synthesis, characterization, and electroluminescent properties of iridium(III) 2-phenylpyridine-type complexes containing trifluoromethyl substituents and various main-group moieties
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New heteroleptic cyclometalated iridium(III) 2-phenylpyridine-type complexes with trifluoromethyl substituents and various main-group moieties were synthesized and their photophysical, electrochemical, and electroluminescent (EL) properties studied. The emission color can be tuned by a facile derivatization of the phenyl moiety of 2-phenylpyridine with various main-group moieties, and we have prepared new yellowish-green to orange triplet emitters with enhanced charge injection/charge transporting features, which can furnish attractive EL performance in phosphorescent organic light-emitting devices (OLEDs). Attempts were also made to fabricate two-color white-light OLEDs based on a combination of fluorescent blue and phosphorescent orange emitters.
- Ho, Cheuk-Lam,Lam, Ching-Shan,Sun, Ning,Ma, Dongge,Liu, Li,Yu, Zhen-Qiang,Xue, Liqin,Lin, Zhenyang,Li, Hua,Lo, Yih Hsing,Wong, Wai-Yeung
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p. 999 - 1014
(2014/08/18)
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- Novel multifunctional organic semiconductor materials based on 4,8-substituted 1,5-naphthyridine: Synthesis, single crystal structures, opto-electrical properties and quantum chemistry calculation
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A series of 4,8-substituted 1,5-naphthyridines (1a-1h) have been successfully synthesised by a Suzuki cross-coupling between 4,8-dibromo-1,5- naphthyridine (4) and the corresponding boronic acids (2a-2h) in the presence of catalytic palladium acetate in yields of 41.4-75.8% and have ben well characterized. They are thermally robust with high phase transition temperatures (above 186 °C). Compounds 1b, 1e and 1f crystallized in the monoclinic crystal system with the space groups P21/c, P21/c and P21/n, respectively. All of them show the lowest energy absorption bands (λmaxAbs: 294-320 nm), revealing low optical band gaps (2.77-3.79 eV). These materials emit blue fluorescence with λmaxEm ranging from 434-521 nm in dilute solution in dichloromethane and 400-501 nm in the solid state. 4,8-Substituted 1,5-naphthyridines 1a-1h have estimated electron affinities (EA) of (2.38-2.72 eV) suitable for electron-transport materials and ionization potentials (IP) of 4.85-5.04 eV facilitate excellent hole-injecting/hole-transport materials properties. Quantum chemical calculations using DFT B3LYP/6-31G* showed nearly identical the lowest unoccupied molecular orbitals (LUMO) of -2.39 to -2.19 eV and the highest occupied molecular orbitals (HOMO) of -5.33 to -6.84 eV. These results demonstrate the 4,8-substituted 1,5-naphthyridines 1a-1h with a simple architecture might be promising blue-emitting (or blue-green-emitting) materials, electron-transport materials and hole-injecting/hole-transport materials for applications for developing high-efficiency OLEDs.
- Wang, Kun-Yan,Chen, Chen,Liu, Jin-Fang,Wang, Qin,Chang, Jin,Zhu, Hong-Jun,Li, Chong
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p. 6693 - 6704
(2012/09/22)
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- Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components
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(Chemical Equation Presented) Step by step: Highly selective cross dehydrogenase arylation of acetanilides was developed to construct biaryls under mild condition. With this method, different aryl C-H bonds were activated in sequential reactions to construct functionalized carbazoles (see scheme), which are present as key structural units in various biological molecules and organic optical materials.
- Li, Bi-Jie,Tian, Shi-Liang,Fang, Zhao,Shi, Zhang-Jie
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p. 1115 - 1118
(2008/09/21)
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- Pyrazolopyrimidines as therapeutic agents
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The present invention is directed to pyrazolopyrimidine derivatives of formula (I) wherein the substituents are defined herein, which are useful as kinase inhibitors and as such are useful for affecting angiogenesis and diseases and conditions associated with angiogenesis.
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- Pyrazolopyrimidines as therapeutic agents
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The present invention provides compounds of Formula I, including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R2, and R3 are defined as described herein.
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- Alkenyl- and alkynl-containing metalloprotease inhibitors
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Disclosed are compounds which are inhibitors of metalloproteases and which are effective in treating conditions characterized by excess activity of these enzymes. In particular, the compounds have a structure according to the following Formula (I): where X, W, Z, A, G, R1, R2, R3, R4, R5, R5′and k have the meanings described in the specification. This invention also includes optical isomers, diastereomers and enantiomers of the formula above, and pharmaceutically-acceptable salts, biohydrolyzable amides, esters, and imides thereof Also described are pharmaceutical compositions comprising these compounds, and methods of treating or preventing metalloprotease-related maladies using the compounds or the pharmaceutical compositions.
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- Thermotropic and lyotropic liquid crystalline phases of rigid aromatic amphiphiles
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Rodlike amphiphilic molecules that contain exclusively aromatic building-blocks and no flexible alkyl chains have been synthesized and their mesomorphic properties investigated. These novel compounds bear diol head groups of different size (2,3-dihydroxypropyloxy or 5,6-dihydroxy-3-oxahexyloxy groups) at one end of a biphenyl unit, various aromatic segments (benzyloxy, 4-, 3-, or 2-methylbenzyloxy, phenoxy groups) at the other, and additional methyl substituents in different positions. They were synthesized by using Suzuki cross-coupling reactions as the key steps. Their thermotropic mesomorphism was investigated by means of polarized light optical microscopy, differential scanning calorimetry, and, for enantiotropic phases, by X-ray scattering. The liquid crystallinity of this class of compounds is influenced by protic solvents, such as water and glycerol. Dependent on the temperature and the solvent content, different SA phases were found. Several mesophases resulting from the frustration of these layer structures (e.g., different columnar phases, optical isotropic mesophases, and nematic phases) were also present. The smectic phases have different degrees of intercalation (SAd, SA2). The columnar phases are supposed to be ribbon structures that result from the collapse of the smectic layers. They occur in some pure compounds or they are induced upon the addition of protic solvents. The particular phase sequences of the different compounds depend mainly on the position of the methyl substituents at the biphenyl cores and are largely determined by the degree of intercalation of the aromatic cores.
- Koelbel, Marius,Beyersdorff, Tom,Tschierske, Carsten,Diele, Siegmar,Kain, Jens
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p. 3821 - 3837
(2007/10/03)
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