- Rh(III)-Catalyzed Annulation of 2-Biphenylboronic Acid with Diverse Activated Alkenes
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Rhodium(III)-catalyzed annulation of 2-biphenylboronic acids with three classes of activated alkenes has been realized, leading to the synthesis of fused or bridged cyclic skeletons via transmetalation-initiated C-H activation. In the annulative coupling of 2-biphenylboronic acid with a CF3-substituted enone, the bulky cyclopentadienyl ligand (CptBu) in the catalyst proved effective to promote the reductive elimination process prior to protonolysis, affording the [4 + 2] annulated products instead of the simple 1,4-addition product. Seven-membered rings were obtained when disubstituted cyclopropenones were employed. Bridged cycles were isolated from the coupling of 2-biphenylboronic acid with benzoquinones as a result of 2-fold Michael additions. The substrate scopes were found to be broad with up to 99% yield under air-tolerant conditions.
- Chang, Junbiao,Dong, Zhenzhen,Li, Xingwei,Liu, Bingxian,Yang, Lingyun
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p. 7199 - 7204
(2021/09/22)
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- Preparation method of triphenylene derivative
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The invention relates to the field of organic chemistry, and in particular, relates to a preparation method of a triphenylene derivative. The invention provides the preparation method of the triphenylene derivative, wherein the method comprises the step: carrying out cyclization reaction on a compound represented by a formula 4 in the presence of acid, an initiator and an oxidant to provide a compound represented by a formula 5. According to the preparation method of the triphenylene derivative, provided by the invention, arylation reaction is carried out by using the acid and the oxidant, sothat side reactions generated in the reaction are few, the overall conversion rate of the reaction is high, and the raw materials are economical and practical; and in addition, the whole reaction route has high reaction yield and is convenient for industrial production and operation, and good industrialization prospects are realized.
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Paragraph 0099-0106
(2021/03/31)
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- Ag-Catalyzed Cyclization of Arylboronic Acids with Elemental Selenium for the Synthesis of Selenaheterocycles
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A general method for the synthesis of five-membered and six-membered selenaheterocycles through Ag-catalyzed C?Se bond-forming reaction is reported. This reaction proceeds via intramolecular cyclization of arylboronic acids with selenium powder. Preliminary mechanism studies demonstrate that this transformation involves a selenium-centred radical intermediate. (Figure presented.).
- Gao, Wen-Xia,Huang, Xiao-Bo,Liu, Miao-Chang,Wu, Hua-Yue,Zhang, Xue,Zhou, Yun-Bing
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p. 5639 - 5644
(2020/11/30)
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- Aryl boronic acid preparation method
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The invention belongs to the technical field of fine chemical engineering, and relates to an aryl boronic acid preparation method. In the prior art, aryl boronic acid as a novel safe and environmentally-friendly arylation reagent is widely used in scientific research and production of various fine chemicals containing aryl structures in the fields of medicines, pesticides, advanced materials and the like; and the aryl boronic acid compound preparation method reported in the disclosed literature has problems of harsh reaction conditions and high cost. A purpose of the invention is to provide amethod, wherein an aryl boron compound is formed by carrying out a reaction on a Grignard reagent and trialkyl borate under mild conditions, the composition of the aryl boron compound is converted from the main component diaryl borate into the main component aryl borate, and the aryl borate is hydrolyzed to obtain aryl boric acid, so that the preparation cost of the acyl aryl boric acid compound can be remarkably reduced, and the method has good practical application prospect.
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Paragraph 0033-0036; 0040
(2020/01/25)
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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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- Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes
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A copper-mediated method for the transformation of diverse arylboron compounds and arylstannanes to aryl-[11C]-nitriles is reported. This method is operationally simple, uses commercially available reagents, and is compatible with a wide variety of substituted aryl- and heteroaryl substrates. This method is applied to the automated synthesis of high specific activity [11C]perampanel in 10% nondecay-corrected radiochemical yield (RCY).
- Makaravage, Katarina J.,Shao, Xia,Brooks, Allen F.,Yang, Lingyun,Sanford, Melanie S.,Scott, Peter J. H.
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supporting information
p. 1530 - 1533
(2018/03/23)
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- Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
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A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
- Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
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supporting information
p. 5578 - 5582
(2018/09/25)
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- Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives
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A rhodium-catalyzed annulative coupling of (2-arylphenyl)boronic acids with alkynes has been developed for the facile construction of phenanthrene frameworks. The reaction proceeded without external bases, and dioxygen worked as a terminal oxidant. Deuter
- Nagata, Tomoya,Satoh, Tetsuya,Nishii, Yuji,Miura, Masahiro
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supporting information
p. 1707 - 1710
(2016/07/06)
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- Photocyclodehydrofluorination
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Mallory-type photocyclization involves a series of photoreactions of stilbenes, o-terphenyls and related derivatives, which undergo intramolecular cyclization via dihydrophenanthrene intermediates. In typical Mallory photocyclizations, oxidants are usually needed to produce the final phenanthrene-containing product. In the research described here, appropriately fluorinated stilbenes and o-terphenyls undergo ring closure and HF is eliminated. This photocyclodehydrofluorination (PCDHF) reaction is very useful to produce a wide range of selectively fluorinated polynuclear aromatic hydrocarbons that possess a phenanthrene (or heterocyclic analogue of phenanthrene) substructure. These fluorinated products are of great interest in various aspects of the materials science.
- Li, Zhe,Twieg, Robert J.
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supporting information
p. 15534 - 15539
(2015/11/03)
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- Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis
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An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.
- Mohy El Dine, Tharwat,Erb, William,Berhault, Yohann,Rouden, Jacques,Blanchet, Jér?me
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p. 4532 - 4544
(2015/05/13)
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- Pyrene derivatives comprising heteroaryl amine group and organic light-emitting diode including the same
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The present invention relates to a pyrene derivative represented by chemical formula A, and an organic light-emitting diode including the same. In the chemical formula A, substituents Z, Ar_1, Ar_2, R_1 to R_5, connecting groups L_1 and L_2, and X, m, p and q are the same as defined in a detailed description of the present invention.COPYRIGHT KIPO 2015
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Paragraph 0331; 0441-0446
(2016/10/10)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides a novel compound capable of improving light emitting efficiency, stability and lifespan of an element, an organic electronic element using the same and an electronic device thereof.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2016
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Paragraph 0266; 0275; 0276
(2016/10/07)
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- Sequential one-pot access to molecular diversity through aniline aqueous borylation
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On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.
- Erb, William,Albini, Mathieu,Rouden, Jacques,Blanchet, Jrme
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p. 10568 - 10580
(2015/01/08)
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- Synthesis, self-assembly and photovoltaic applications of tribenzopentaphene derivatives
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Four tribenzopentaphene (TBP) derivatives containing different alkoxy side chains have been synthesized and shown to self-assemble into different microobjects such as microspheres, microfibers and microribbons. Photovoltaic cells of 1b blended with PDI or PC61BM are fabricated and preliminary results show good efficiencies comparable to those of previously reported photovoltaic devices of hexabenzocoronenes. The Royal Society of Chemistry 2013.
- Chou, Ching-En,Li, Yong,Che, Yanke,Zang, Ling,Peng, Zhonghua
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p. 20666 - 20672
(2013/11/06)
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- Morphology control of nanofibril donor-acceptor heterojunction to achieve high photoconductivity: Exploration of new molecular design rule
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Donor-acceptor nanofibril composites have been fabricated, and the dependence of their photocurrent response on the structure and morphology of the donor part has been systematically investigated. The nanofibril composites were composed of template nanofibers, assembled from an electron acceptor molecule, perylene tetracarboxylic diimide (PTCDI), onto which (through drop-casting) various electron donor molecules (D1-D4) were coated. The donor molecules have the same π-conjugated core, but different side groups. Due to the different side groups, the four donor molecules showed distinctly different propensity for intermolecular aggregation, with D1-D3 forming segregated phases, while D4 prefers homogeneous molecular distribution within the film. It was found that the nanofibril composites with D4 exhibit the highest photocurrent, whereas those with aggregation-prone D1-D3 exhibited much lower photocurrent under the same illumination condition. Solvent annealing is found to further enhance the aggregation of D1-D3 but facilitate more uniform molecular distribution of D4 molecules. As a result, the photocurrent response of PTCDI fibers coated with D1-D3 decreased after vapor annealing, whereas those coated with D4 further increased. The detrimental effect of the aggregation of donor molecules on the PTCDI fiber is likely due to the enhanced local electrical field built up by the high charge density around the aggregate-nanofiber interface, which hinders the charge separation of the photogenerated electron-hole pair. The results reported in this study give further insight into the molecular structural effect on photoconductivity of hybrid materials, particularly those based on donor-acceptor composites or interfaces, and provide new molecular design rules and material processing guidelines to achieve high photoconductivity.
- Huang, Helin,Chou, Ching-En,Che, Yanke,Li, Ligui,Wang, Chen,Yang, Xiaomei,Peng, Zhonghua,Zang, Ling
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p. 16490 - 16496
(2013/12/04)
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- Anthranilamide-masked o-iodoarylboronic acids as coupling modules for iterative synthesis of ortho-linked oligoarenes
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Anthranilamide (AAM)-masked o-iodoarylboronic acids were prepared from AAM-masked arylboronic acids via Rucatalyzed o-C-H silylation, followed by iododesilylation with ICl. The Suzuki-Miyaura coupling of AAM-masked o-haloarylboronic acids with arylboronic acids proceeded under ligandfree conditions. Oligo(o-phenylene)s and oligo(naphthalene-2,3-diyl)s were synthesized via iterative Suzuki-Miyaura coupling sequences.
- Koyanagi, Masashi,Eichenauer, Nils,Ihara, Hideki,Yamamoto, Takeshi,Suginome, Michinori
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p. 541 - 543
(2013/06/05)
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- High-color-purity and high-efficiency non-doped deep-blue electroluminescent devices based on novel anthracene derivatives
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Two novel anthracene derivatives 2-tert-butyl-9,10-bis(2-biphenyl) anthracene (TBBPA) and 2-tert-butyl-9,10-bis[2-(1-naphthyl)phenyl]anthracene (TBNPA) were synthesized and characterized. The quantum chemical calculations show that TBBPA and TBNPA have hi
- Wang, Zhi-Qiang,Xu, Chen,Wang, Wei-Zhou,Duan, Lu-Meng,Li, Zhen,Zhao, Bang-Tun,Ji, Bao-Ming
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p. 662 - 667
(2012/05/04)
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- Highly efficient one-pot access to functionalized arylboronic acids via noncryogenic bromine/magnesium exchanges
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A general and convenient protocol for the electrophilic borylation of aryl Grignard reagents prepared from arylbromides by direct insertion of magnesium in the presence of LiCl or by Mg/Br exchange with iPrMgCl?LiCl has been developed. Various aryl boronic acids were synthesized in a straightforward manner in excellent yields at 0 °C.
- Leermann, Timo,Leroux, Frederic R.,Colobert, Francoise
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supporting information; experimental part
p. 4479 - 4481
(2011/10/09)
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- Supramolecular structures and spontaneous resolution: The case of ortho-substituted phenylboronic acids
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The solid state structures of a number of ortho-substituted arylboronic acids, ortho-bromophenyl, ortho-phenylphenyl, pentamethylphenyl, and 10-bromo-9-anthryl, were determined by X-ray diffraction techniques. All boronic acids investigated form dimers in the solid state, but the interconnection of dimers to ribbons differs from that of the parent phenylboronic acid. Pentamethylphenylboronic acid only uses one hydrogen bond but an additional OH-π interaction for connection of dimers, while all others investigated employ two hydrogen bonds for interconnection of dimers to ribbons. 10-Bromo-9-anthrylboronic acid is found to undergo spontaneous resolution of its enantiomers to a racemic conglomerate upon crystallization. The Royal Society of Chemistry.
- Filthaus, Matthias,Oppel, Iris M.,Bettinger, Holger F.
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p. 1201 - 1207
(2008/10/09)
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- ORGANIC ELECTROLUMINESCENT ELEMENT
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The novel compound of the present invention has the diphenylanthracene structure at the center and a specific structure substituted with an aryl group at end portions. The organic electroluminescence device of the present invention comprises a plurality of layers of thin films of organic compounds which comprise a light emitting layer or a plurality of layers comprising a light emitting layer and are disposed between a pair of electrodes and at least one of the layers of thin films of organic compounds comprises the above novel compound. The novel compound exhibits excellent efficiency of light emission and heat resistance, has a long life and emits bluish light having excellent purity of color and the organic electroluminescence device comprises the novel compound and exhibits the same advantageous properties.
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- Substituted phenyl farnesyltransferase inhibitors
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Compounds of formula (I) or pharmaceutically acceptable salts thereof, inhibit farnesyltransferase. Methods for making the compounds, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds are disclosed.
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- Biaryl-pyridoquinazolinone derivatives as anti-cancer agents
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This invention provides a compound having the formula: STR1 wherein: (A) n=2-4; (B) R1 and R2 are the same or different and selected from the group consisting of H, (C1 -C3)alkyl, --CH2 CH2 OH, --CH2 CH2 NH2, and --CH2 CH2 N(CH3)2 or R1 and R2 are alkyl moieties which may taken together to form a 4- to 7-membered ring; (C) R3 is selected from H, --CH3, --CH2 CH3, --CH2 CH2 NH2 ; (D) X is located at the 2-, or 3-position and is selected from the group consisting of 2-naphthyl, 1-naphthyl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, phenyl, and mono- or polysubstituted phenyl wherein the substituents are selected from the group consisting of --OR4, --NR5 R6, (C1 -C3) alkyl, --CF3, F, Cl, Br, I, --NO2, --CN, --SO3 H, --SO2 NR5 R6, --CO2 H, --CO2 R4, and phenyl; R4 is H or (C1 -C4)alkyl; R5 and R6 are the same or different and are selected from H, or (C1 -C4)alkyl, or R5 and R6 are alkyl groups which may be taken together to form a 4-7 membered ring; (E) W is selected from H, --OR4, --NR5 R6, (C1 -C3)alkyl, --CF3, F, Cl, Br, I, --NO2, --CN, --SO2 NR5 R6, --CO2 R4 ; or a pharmacologically acceptable salt thereof which is useful as an antineoplastic agent.
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