- FLUORESCENT COMPOUND AND PREPARATION METHOD AND USE FOR THE SAME
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Disclosed is a fluorescent compound as represented by general formula I, or a salt, an enantiomer, a diastereomer, a tautomer, a solvate or a polymorph thereof, having the structure (I); wherein m and n are each an integer between 0-10; and Y1 and Y2 are each independently selected from the group of hydrogen, phenyl, hydroxyl, carboxyl, an ester group, a boric acid group, a borate group, and a 3 to 7 membered ring substituted with one or more boric acid groups or borate groups, and at least one of Y1 and Y2 is a boron-containing group. The compound has the characteristics of a high fluorescence intensity and a high sensitivity.
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Paragraph 0086
(2021/12/29)
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- 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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- Fluorescent compound and preparation method and application thereof
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The invention discloses a fluorescent compound and a preparation method and application thereof. The fluorescent compound is shown in a general formula I, and the structure of the compound of the formula I is as shown in the description of the fluorescent compound, wherein m and n are each independently an integer from 0-10; and Y and Y are each independently selected from a following group:hydrogen, phenyl, hydroxyl, carboxyl, an ester group, a boric acid group, a boric acid ester group and one or more boric acid group or boric acid ester group substituted 3-7 membered rings, and at least one of Y and Y is a boracic group. The fluorescent compound has the characteristics of high fluorescence intensity and high sensitivity.
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Paragraph 0102-0103
(2019/10/30)
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- New compounds and organic light-emitting diode including the same
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PURPOSE: A compound is provided to improve luminous efficiency and to make low voltage operation possible when applied to an organic electroluminescence device by having low driving voltage and excellent luminous efficiency. CONSTITUTION: A compound is represented by chemical formula 1. In chemical formula 1, each R is selected from hydrogen, deuterium, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C7-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C5-30 cycloalkenyl, substituted or unsubstituted C1-30 alkoxy, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C1-30 alkylthioxy, substituted or unsubstituted C5-30 arylthioxy, substituted or unsubstituted C1-30 alkylamine, substituted or unsubstituted C5-30 arylamine, substituted or unsubstituted C5-50 aryl, substituted or unsubstituted C3-50 heteroaryl, substituted or unsubstituted silicon, substituted or unsubstituted boron, substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, hydroxy, nitro, halogen, amide, and ester.
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Paragraph 0200-0206
(2019/08/30)
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- Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids
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Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.
- Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu
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p. 164 - 171
(2018/12/05)
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- Regioselective Synthesis of o-Benzenediboronic Acids via Ir-Catalyzed o-C-H Borylation Directed by a Pyrazolylaniline-Modified Boronyl Group
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Ir-catalyzed ortho-directed C-H borylation of pyrazolylaniline (PZA)-modified arylboronic acids with bis(pinacolate)diboron afforded o-benzenediboronic acids in which two boronyl groups are differentially modified by pinacol (PIN) and PZA. By using this borylation after nondirected Ir-catalyzed C-H borylation, o-benzenediboronic acids are conveniently synthesized from unfunctionalized arenes. The differentially modified o-benzenediboronic acids undergo selective oxidation and Suzuki-Miyaura cross-coupling at the PZA-modified boronyl groups, affording o-functionalized arylboronic acids selectively.
- Yamamoto, Takeshi,Ishibashi, Aoi,Suginome, Michinori
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supporting information
p. 886 - 889
(2017/02/26)
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- Preparation method for 3-carboxyphenylboronic acid
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The invention discloses a preparation method for 3-carboxyphenylboronic acid, relating to the technical field of organic synthesis. The preparation method comprises the steps of performing Grignard reaction on m-bromomethyl benzene, magnesium scraps and iodine by using the m-bromomethyl benzene as a starting material, so as to generate a Grignard reagent, performing boronated reaction on the Grignard reagent and trimethyl borate so as to prepare 3-Tolylboronic acid, and oxidizing the 3-Tolylboronic acid with potassium permanganate in an alkaline condition so as to prepare 3-carboxyphenylboronic acid. According to the preparation method, cheap m-bromomethyl benzene easy to obtain is used as the starting material, the 3-carboxyphenylboronic acid is prepared through Grignard reaction, boronated reaction and oxidization reaction, the operations are simple, the average purity of the product 3-carboxyphenylboronic acid reaches 99.3%, and the average total yield reaches 50%. The product yield and purity are ensured at low cost, so that the preparation method is applicable to industrial production.
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Paragraph 0009; 0020; 0023; 0026
(2017/08/31)
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- Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts
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We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.
- Mfuh, Adelphe M.,Doyle, John D.,Chhetri, Bhuwan,Arman, Hadi D.,Larionov, Oleg V.
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supporting information
p. 2985 - 2988
(2016/03/19)
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- Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles
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Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.
- Yasukawa, Tomohiro,Kuremoto, Tatsuya,Miyamura, Hiroyuki,Kobayashi, Sh?
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supporting information
p. 2716 - 2718
(2016/06/15)
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- Transition-metal-free synthesis of phenanthridinones from biaryl-2-oxamic acid under radical conditions
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Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products. (Chemical Equation Presented).
- Yuan, Ming,Chen, Li,Wang, Junwei,Chen, Shenjie,Wang, Kongchao,Xue, Yongbo,Yao, Guangmin,Luo, Zengwei,Zhang, Yonghui
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supporting information
p. 346 - 349
(2015/02/19)
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- Mn-catalyzed aromatic C-H alkenylation with terminal alkynes
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The first manganese-catalyzed aromatic C-H alkenylation with terminal alkynes is described. The procedure features an operationally simple catalyst system containing commercially available MnBr(CO)5 and dicyclohexylamine (Cy2NH). The reaction occurs readily in a highly chemo-, regio-, and stereoselective manner delivering anti-Markovnikov E-configured olefins in high yields. Experimental study and DFT calculations reveal that (1) the reaction is initiated by a C-H activation step via the cooperation of manganese and base; (2) manganacycle and alkynylmanganese species are the key reaction intermediates; and (3) the ligand-to-ligand H-transfer and alkynyl-assisted C-H activation are the key steps rendering the reaction catalytic in manganese.
- Zhou, Bingwei,Chen, Hui,Wang, Congyang
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supporting information
p. 1264 - 1267
(2013/03/14)
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- SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS
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Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.
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Paragraph 0102-0103; 0107
(2013/03/26)
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- Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation
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A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.
- Wang, Congyang,Rakshit, Souvik,Glorius, Frank
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supporting information; experimental part
p. 14006 - 14008
(2010/12/24)
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- Efficient hydrolysis of organotrifluoroborates via silica gel and water
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(Chemical Equation Presented) A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates.As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters. 2009 American Chemical Society.
- Molander, Gary A.,Cavalcanti, Livia N.,Canturk, Belgin,Pan, Po-Shen,Kennedy, Lauren E.
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supporting information; experimental part
p. 7364 - 7369
(2010/01/16)
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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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- Iridium(I)-salicylaldiminato-cyclooctadiene complexes used as catalysts for phenylborylation
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Iridium(I) salicylaldiminato-cyclooctadiene complexes, Ir(-o-O-C6H4-CH{double bond, long}N-R)(cod) (R = CH2Ph (1), Ph (2); cod = 1,5-cyclooctadiene), have been prepared, characterized and used as catalysts for arylborylation via C-H activation. With 1 as a catalyst, isolated yields of up to 91% has been achieved for the borylation of benzene by bis(pinacolato)diboron in the presence of tetra-2-pyridinylpyrazine and an ionic liquid. The catalytic system could be recycled for at least three times without loss of activity.
- Yinghuai, Zhu,Yan, Koh Cheng,Jizhong, Luo,Hwei, Chong Siow,Hon, Yong Chun,Emi,Zhenshun, Su,Winata, Monalisa,Hosmane, Narayan S.,Maguire, John A.
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p. 4244 - 4250
(2008/02/13)
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- Benzoxepin-derived estrogen receptor modulators: A novel molecular scaffold for the estrogen receptor
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We present and examine the efficacy of a novel benzoxepin-based scaffold for modulation of the human estrogen receptor. Receptor tolerance of this new molecular scaffold is examined through presentation of experimentally determined antiproliferative effects on human MCF-7 breast tumor cells and measured binding affinities. The effect of functional group substitution on the benzoxepin scaffold is explored through a brief computational structure - activity relationship investigation with molecular simulation.
- Lloyd, David G.,Hughes, Rosario B.,Zisterer, Daniela M.,Williams, D. Clive,Fattorusso, Caterina,Catalanotti, Bruno,Campiani, Giuseppe,Meegan, Mary J.
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p. 5612 - 5615
(2007/10/03)
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- Deprotection of pinacolyl boronate esters by transesterification with polystyrene-boronic acid
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A mild, efficient method for the deprotection of pinacolyl organoboronate esters is described. Treatment of the organoboronate ester with excess polystyrene-boronic acid followed by filtration and evaporation of the solvent provides the corresponding organoboronic acid. Mild deprotection of pinacolyl boronate esters to the corresponding boronic acids was achieved in the presence of excess polystyrene-boronic acid via a transesterification process. The procedure allows for the cleavage of pinacolyl boronate esters in the presence of sensitive functional groups. Crown Copyright
- Pennington, Thomas E.,Kardiman, Cynantya,Hutton, Craig A.
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p. 6657 - 6660
(2007/10/03)
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- A new method for installation of aryl and alkenyl groups onto a cyclopentene ring and synthesis of prostaglandins
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To construct a new strategy for synthesis of cyclopentanoids, the transition metal-catalyzed coupling reaction of cis 4-cyclopentene-1,3-diol monoacetate 1 with hard nucleophiles, RT-m, was investigated (eq 1 in Chart 1). Although preliminary experiments using PhZnCl, PhSnMe3, [Ph-B(Me)(OCH-(Me)CH(Me)O)]-Li+ (6a) (derived from boronate ester 4a (RT = Ph) and MeLi) in the presence of a palladium or a nickel catalyst resulted in production of unidentified compounds, enone 16, and/or ketone 17 or recovery of 1, a new borate 5a (derived from 4a and n-BuLi) in the presence of a nickel catalyst (NiCl2(PPh3)2) in THF at room temperature furnished the trans coupling products 2a (RT = Ph) and 3a (RT = Ph) in high combined yield, but with a low product ratio of 0.9:1. The ratio was improved to 13:1 by addition of t-BuCN and NaI into the reaction mixture. This is the first successful example of the reaction of 1 with a hard nucleophile, and the increase in the ratio, realized with the additives, is unprecedented. This reagent system (borate 5 (1.2-1.8 equiv), NiCl2-(PPh3)2 (5-10 mol%), t-BuCN (2-5 equiv), NaI (0.5-1 equiv), THF, room temp) was further investigated with aryl borates 5b-g and alkenyl borates 5h-n to afford 2b-n in moderate to good yields (52-89%) with practically acceptable levels of the regioselectivity (5 ~ 21:1), thus establishing the generality of the reaction (Table 2, eqs 6 and 7). Starting with the products of the coupling reaction, syntheses of the prostaglandin intermediates 13 and 14 (for 11-deoxy-PGE2 and PGA2) and Δ7-PGA1 methyl ester (15) were accomplished efficiently. During these investigations, LDA, LiCA, and LHMDS were found to be equally efficient bases for aldol reaction at the α′ (α prime) position of cyclopentenones 39, 40, and 41 (Table 3).
- Kobayashi, Yuichi,Murugesh, Modachur G.,Nakano, Miwa,Takahisa, Eisuke,Usmani, Shahid B.,Ainai, Takayuki
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p. 7110 - 7123
(2007/10/03)
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- Triaromatic compounds and pharmaceutical/cosmetic compositions comprised thereof
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Novel pharmaceutically/cosmetically-active triaromatic compounds have the structural formula (I): and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
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- TETRACYCLIC COMPOUNDS AS DOPAMINE AGONISTS
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A tetracyclic compound of the formula: STR1 wherein A and the atoms to which it is attached and the optional double bond represent a mono-or di-heterocyclic ring selected from: STR2 wherein R 1, R. sup.2, R 3, R 4 and X are specifically defined, which compounds are useful in the treatment of dopamine-related neurological, psychological and cardiovascular disorders as well as in the treatment of substance abuse and other addictive behavior disorders, cognitive impairment and attention deficit disorder.
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- Boronic acid adducts of metal dioxime complexes useful in labelling proteins and other amine-containing compounds
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Boronic acid adducts of metal dioxime complexes are useful as reagents for labeling proteins and other amine-containing compounds.
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- REACTIONS OF DIBORANE WITH LITHIUM DIARYLCUPRATES AND ORGANOCADMIUM COMPOUNDS
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Lithium diarylcuprates react with diborane to form as intermediates organoboron compounds, which can be converted into phenols, arylboronic acids and arylamines; complexes of triarylboron compounds can also be isolated.Preliminary studies show that organo
- Bullen, N. P.,Chiheru, K. S.,Thorpe, F. G.
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p. 147 - 154
(2007/10/02)
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