- Regioselectivity in metallation reactions of 2-(2'-naphthyl)pyridine: 1'-versus 3'-reactivity in mercuration and palladation reactions. Crystal structure of chloro(pyridine)3,N>palladium
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Regioselectivity is found to vary with the reagent in cyclometallation reactions of 2-(2'-naphthyl)pyridine.Mercuration produces a mixture of 1'- and 3'-naphthyl metallated species with the 1'-substituted material as the major product.Palladation results in clean 3'-naphthyl metallation, as confirmed by the crystal structure of the pyridine derivative chloro(pyridine)3,N>palladium. Keywords: Mercury; Palladium; Cyclometallation; Crystal structure
- Ford, Alan,Sinn, Ekkehard,Woodward, Simon
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Read Online
- Synthesis and photophysical processes of 9-bromo-10-naphthalen-2-yl-anthracene
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A novel luminescent compound, 9-bromo-10-naphthalen-2-yl-anthracene (BNA) is synthesized by Suzuki Cross-coupling reaction of 9-bromo-anthracene and naphthalene-2-boronic acid. The structure is characterized by 1H NMR, IR and UV-vis spectroscopy. The photophysical processes of 9-bromo-10-naphthalen-2-yl-anthracene have been carefully investigated by UV-vis absorption and fluorescence spectra. The results show that the compound emits blue and blue-violet light. The emission spectra exhibit obvious solvent effect. With the difference in polarity of solvents, The emission spectra is not only slightly blue shift with the increase of the solvent polarity but also change on the intensity of fluorescence at room temperature .The light emitting can be quenched by electron donor, N,N-dimethylaniline (DMA). On adding gradually DMA into the solution of BNA, the emission intensities of fluorescence are gradually decreased. The quenching effect follows the Stern-Volmer equation.
- Guo, Zhiqiang,Jin, Shuo,Liu, Bo
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Read Online
- Highly twisted pyrene derivatives for non-doped blue OLEDs
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New highly twisted rigid blue light-emitting materials were designed, composed of pyrene with a xylene core unit and either naphthalene or phenyl end units. These blue-emitting materials were synthesized via the Suzuki cross-coupling reaction and their structures were confirmed using FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. The optical, electrochemical and thermal properties of the materials were investigated. The non-coplanar structure introduced by highly twisted xylene units provides steric hindrance, resulting in very deep blue emission. The fabricated devices exhibited a maximum external quantum efficiency (EQE) of 3.69% with CIE color coordinates (x, y: 0.15, 0.06).
- Lee, Sang Bong,Park, Kwang Hun,Joo, Chul Woong,Lee, Jeong-Ik,Lee, Jonghee,Kim, Yun-Hi
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Read Online
- Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols
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Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.
- Mayr, Stefanie,Marin-Luna, Marta,Zipse, Hendrik
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p. 3456 - 3489
(2021/03/01)
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- Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties
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A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.
- Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto
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supporting information
p. 13613 - 13623
(2021/08/23)
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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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- BORON DIIODIDE COMPOUND, AND BORONIC ACID, BORONIC ESTER AND THE LIKE OBTAINED THEREFROM, AND PRODUCTION METHOD OF THEM
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PROBLEM TO BE SOLVED: To provide a method which enables simple production of a boronic acid, a boronic ester compound or the like suitable for production of various compounds. SOLUTION: The problem is solved by a boron diiodide compound represented by the following general formula (Y). (In the formula (Y), Ar is an n-valent heteroaryl ring, aryl ring having 10 or more carbon atoms, or substituted benzene ring, where at least one hydrogen atom in these rings may be substituted; n is an integer from 1 to 6; and at least one hydrogen atom in the compound represented by the formula (Y) may be substituted with deuterium.) COPYRIGHT: (C)2019,JPO&INPIT
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Paragraph 0258
(2019/05/10)
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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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- Naphtho-fluorene carbazole compound and application thereof
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The invention belongs to the field of organic electroluminescence, and in particular relates to a naphtho-fluorene carbazole compound and application thereof. An OLED device manufactured by taking thesynthesized organic compound as a main body light-emitting material can be applied in the fields of AM drive OLED display, PM drive OLED display or OLED illumination. The external quantum efficiency,the power efficiency and the current efficiency of the device are greatly improved, and the service life of the device is obviously prolonged, so that the naphtho-fluorene carbazole compound has thegood market prospect.
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Paragraph 0050; 0053; 0054; 0055
(2018/03/26)
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- CH activation-based transformation of naphthalenes to 3-iodo-2-naphthylboronic acid derivatives for use in iterative coupling synthesis of helical oligo(naphthalene-2,3-diyl)s
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Oligo(naphthalene-2,3-diyl)s were synthesized by iterative cross-coupling of 1,8-diaminonaphthalene-modified 3-iodo- 2-naphthylboronic acids prepared from naphthalenes via Ircatalyzed CH borylation, Ru-catalyzed ortho-CH silylation directed by an anthrani
- Yamamoto, Takeshi,Ishibashi, Aoi,Koyanagi, Masashi,Ihara, Hideki,Eichenauer, Nils,Suginome, Michinori
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supporting information
p. 604 - 606
(2017/06/19)
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- BLUE FLUORESCENT HOST MATERIALS, AND ORGANIC THIN FILM AND ORGANIC LIGHT EMITTING DEVICES COMPRISING THE SAME
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The present invention provides an organic compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. The present invention comprises a blue fluorescent host material, thereby providing the organic electroluminescent device having improved driving voltage, light-emitting efficiency, and light-emitting lifespan.COPYRIGHT KIPO 2017
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Paragraph 0110-0114
(2017/06/19)
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- Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation
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Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.
- Jiang, Min,Yang, Haijun,Fu, Hua
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supporting information
p. 5248 - 5251
(2016/11/02)
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- Novel anthracene derivatives and organic electroluminescent device using the same
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The present invention relates to a novel asymmetric anthracene derivative and an organic light-emitting diode including the same in a light-emitting layer. More specifically, the anthracene derivative, according to the present invention, is a highly-twisted asymmetric anthracene compound.
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Paragraph 0063-0066
(2016/12/01)
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- Anthracene-based compounds and Organic light emitting device comprising the same
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Disclosed are an anthracene-based compound and an organic light emitting device. The anthracene-based compound has high thermal stability and excellent optical properties and chemical properties to provide high quality blue organic light emitting device.
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Paragraph 0266; 0267; 0274; 0275
(2016/10/27)
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- Anthracene-based compounds and Organic light-emitting device comprising the same
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Disclosed are an anthracene-based compound and an organic light emitting device. The anthracene-based compound has high thermal stability and excellent optical properties and chemical properties to provide high quality blue organic light emitting device. Disclosed in another embodiment of the present invention is an organic light emitting device which includes a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, and including a light emitting layer, wherein the organic layer includes one or more kind among the anthracene-based compounds.COPYRIGHT KIPO 2015
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Paragraph 0299; 0300; 0301; 0302
(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 0267-0270
(2016/10/07)
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- The organic light emitting element and heterocyclic compound containing same
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A heterocyclic compound of formula 1 and an organic light-emitting device including an organic layer containing the heterocyclic compound. The heterocyclic compound of Formula 1 may be suitable as a material for an emission layer, an electron transport la
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Paragraph 0092-0094
(2016/10/08)
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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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- Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand
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The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh) 3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by Hbonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4′- and 8,8′-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7′-positions have the biggest impact in a positive direction. VANOL destination: The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate; see figure) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Copyright
- Guan, Yong,Ding, Zhensheng,Wulff, William D.
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supporting information
p. 15565 - 15571
(2013/11/19)
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- Synthesis and characterization of highly soluble blue emitting poly(2-vinylanthracene) with 9,10-di(2-naphthalenyl) and 9,10-di(3-quinolinyl) substituents
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Two new blue fluorescent polymers poly(910-di(2-naphthalenyl)-2- vinylanthracene) (P(2ADN)) and poly(9,10-di(3-quinolinyl)-2-vinylanthracene) (P(3ADQ)), were polymerized from free radical solution addition polymerization with Mn = 21,500 and 15,400, respectively. The polymers are highly soluble in common organic solvents while P(3ADQ) is also soluble in polar solvents including a 1/1 mixture of ethanol/water. Both polymers are amorphous with excellent thermal stability (Tg (Midpoint) = 343 C and 298 C for P(2ADN) and P(3ADQ), respectively). P(2ADN) exhibited three prominent absorption bands in tetrahydrofuran (364, 383 and 403 nm) and is similar to that of P(3ADQ) (369, 384 and 404 nm). The solid-state Commission Internationale d'Eclairage (CIEx,y) color coordinates for illumination were (0.15, 0.10) for P(2ADN) and (0.15, 0.13) for P(3ADQ) which lied within the requirements for a true blue display color. The photoluminescence (PL) of the polymers red-shifted 16-17 nm from their respective pendant chromophore 2-methyl-9,10-di(2-naphthalenyl)anthracene (2MADN) and 2-methyl-9,10-di(3- quinolinyl)anthracene (3MADQ) and can be attributed to partial π-π stacking between the adjacent aromatic pendant groups in the polymer chains. The luminescences of 3MADQ and P(3ADQ) are sensitive to pH and the pKa for the alkalescent 3MADQ and P(3ADQ) calculated was 2.4 and 2.7, respectively. Both polymers have similar band-gap energy (Eg) between 2.88 and 2.91 eV, while the LUMO/HOMO for P(3ADQ) is shifted slightly downward -0.06 to -0.03 eV compared to P(2ADN). The mobility (μhole) of the two polymers were measured to be 4.0 × 10-7 and 10-8 cm 2/(V-s) for P(2ADN) and P(3ADQ), respectively.
- Wang, Jianli,Leung, Louis M.
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p. 105 - 115
(2013/10/21)
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- Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]
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Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.
- Molander, Gary A.,Cavalcanti, Livia N.,Garcia-Garcia, Carolina
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p. 6427 - 6439
(2013/07/26)
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- Organotrifluoroborate hydrolysis: Boronic acid release mechanism and an acid-base paradox in cross-coupling
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The hydrolysis of potassium organotrifluoroborate (RBF3K) reagents to the corresponding boronic acids (RB(OH)2) has been studied in the context of their application in Suzuki-Miyaura coupling. The "slow release" strategy in such SM couplings is only viable if there is an appropriate gearing of the hydrolysis rate of the RBF3K reagent with the rate of catalytic turnover. In such cases, the boronic acid RB(OH)2 does not substantially accumulate, thereby minimizing side reactions such as oxidative homocoupling and protodeboronation. The study reveals that the hydrolysis rates (THF, H2O, Cs2CO 3, 55 °C) depend on a number of variables, resulting in complex solvolytic profiles with some RBF3K reagents. For example, those based on p-F-phenyl, naphthyl, furyl, and benzyl moieties are found to require acid catalysis for efficient hydrolysis. This acid-base paradox assures their slow hydrolysis under basic Suzuki-Miyaura coupling conditions. However, partial phase-splitting of the THF/H2O induced by the Cs2CO 3, resulting in a lower pH in the bulk medium, causes the reaction vessel shape, material, size, and stirring rate to have a profound impact on the hydrolysis profile. In contrast, reagents bearing, for example, isopropyl, β-styryl, and anisyl moieties undergo efficient "direct" hydrolysis, resulting in fast release of the boronic acid while reagents bearing, for example, alkynyl or nitrophenyl moieties, hydrolyze extremely slowly. Analysis of B-F bond lengths (DFT) in the intermediate difluoroborane, or the Swain-Lupton resonance parameter (R) of the R group in RBF3K, allows an a priori evaluation of whether an RBF3K reagent will likely engender "fast", "slow", or "very slow" hydrolysis. An exception to this correlation was found with vinyl-BF 3K, this reagent being sufficiently hydrophilic to partition substantially into the predominantly aqueous minor biphase, where it is rapidly hydrolyzed.
- Lennox, Alastair J. J.,Lloyd-Jones, Guy C.
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p. 7431 - 7441
(2012/06/16)
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- High efficient and high color pure blue light emitting materials: New asymmetrically highly twisted host and guest based on anthracene
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New asymmetrically highly twisted anthracene derivatives serve as a matched host and guest material in high efficiency blue OLEDs. 2-(2- Methylnaphtathalene-1-yl)-9,10-di(naphthalene-2-yl)anthracene and N-(4-(10-naphthalene-2-yl)anthracene-9-yl)phenyl-N-p
- Kang, Il,Back, Jang-Yeol,Kim, Ran,Kim, Yun-Hi,Kwon, Soon-Ki
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experimental part
p. 588 - 595
(2012/02/01)
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- Iron trichloride promoted hydrolysis of potassium organotrifluoroborates
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In the presence of iron trichloride, the hydrolysis of potassium organotrifluoroborates occurs smoothly at room temperature to afford the corresponding organoboronic acids in good to excellent yields. The hydrolysis is effective for aryltrifluoroborates as well as alkenyl- and alkyl- trifluoroborates.
- Blevins, David W.,Yao, Min-Liang,Yong, Li,Kabalka, George W.
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experimental part
p. 6534 - 6536
(2011/12/22)
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- Deep-blue and white organic light-emitting diodes based on novel fluorene-cored derivatives with naphthylanthracene endcaps
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Novel fluorene based deep-blue-emitting molecules with naphthylanthracene endcaps, namely 2,7-di(10-naphthylanthracene-9-yl)-9,9-dioctylfluorene (NAF1) and 7,7′-di(10-naphthylanthracene-9-yl)-9,9,9′,9′-tetraoctyl- 2,2′-bifluorene (NAF2), are synthesized by a Suzuki cross-coupling reaction. These materials exhibit excellent thermal and amorphous stabilities, and high fluorescence quantum yield of over 70%. Organic light-emitting devices (OLEDs) using NAF1 or NAF2 as non-doped emitter exhibit bright deep blue electroluminescence with CIE coordinates of (0.15, 0.13) for NAF1, (0.16, 0.13) for NAF2. A maximum power efficiency of 2.2 lm W-1 (4.04 cd A -1, 4.04%) is achieved for NAF1, which is among the highest values ever reported for deep-blue fluorescent OLEDs. A further improved coordinates of (0.15, 0.09) with efficiencies of 3.56 cd A-1 and 2.10 lm W -1 are achieved for NAF1 upon tuning device thickness, which are also among the best data for non-doped deep blue fluorescent OLEDs with a CIE coordinate of y -1 (7.66 cd A -1), a brightness of 12090 cd m-2, and a standard white light coordinates of (0.33, 0.33). This performance is among the best results ever reported for two-emitting-component white OLEDs based on fluorescent materials.
- Zhang, Ting,Liu, Di,Wang, Qian,Wang, Renjie,Ren, Huicai,Li, Jiuyan
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scheme or table
p. 12969 - 12976
(2011/12/21)
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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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- A recyclable Au(I) catalyst for selective homocoupling of arylboronic acids: Significant enhancement of nano-surface binding for stability and catalytic activity
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Au nanoparticles stabilized by polystyrene-co-polymethacrylic acid microspheres (PS-co-PMAA) were prepared and characterized via X-ray diffraction (XRD), and transmission electron microscope (TEM). The Au nanoparticles supported on the microspheres showed highly selective catalytic activity for homo-coupling reactions of arylboronic acids in a system of aryl-halides and arylboronic acids. X-ray photoelectron spectroscopy (XPS) spectra of the catalyst shows large amounts of Au(l) complexes band to the surface of the Au nanoparticles, which contributes to the selective homocoupling of the arylboronic acids. More importantly, this supported Au complex is a highly recyclable catalyst. The supported Au catalyst can be recycled and reused at least 6 times for a phenylboronic acid reactant, whereas the parent complex shows very low catalytic activity for this compound. The high catalytic activity of this material is attributed to: (1) the high surface to volume ratio which leads to more active sites being exposed to reactants; (2) the strong surface binding of the Au nanoparticle to the Au(1) complexes, which enhances both the stability and the catalytic activity of these complexes. Copyright
- Zhang, Xin,Zhao, Haitao,Wang, Jianhui
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experimental part
p. 5153 - 5160
(2011/12/15)
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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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- Organic glass-forming materials: 1,3,5-Tris(naphthyl)benzene derivatives
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(Chemical Equation Presented) The organic glass-forming materials 1,3-bis(1-naphthyl)-5-(2-naphthyl)benzene (2) and its partially deuterated analogue, 1,3-bis(1-naphthyl-d7)-5-(2-naphthyl)benzene (2-d 14), have been synthesized on a gram scale using Suzuki coupling reactions. Detailed spectroscopic studies afford complete NMR assignments ( 1H, 2H, 13C) for both compounds. Modest energy barriers for the interconversion of atropisomers (ca. 15 kcal/mol) result in a propensity for these materials to form supercooled liquids and glasses, rather than undergoing crystallization. The preparation of these materials enables detailed studies of physical properties of organic glasses and molecular diffusion in condensed phases.
- Bonvallet, Paul A.,Breitkreuz, Caroline J.,Yong, Seol Kim,Todd, Eric M.,Traynor, Katherine,Fry, Charles G.,Ediger,McMahon, Robert J.
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p. 10051 - 10057
(2008/04/05)
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- Asymmetric construction of chiral C-N axes through rhodium-catalyzed 1,4-addition
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Catalytic asymmetric construction of chiral C-N axes has been developed through a rhodium-catalyzed asymmetric 1,4-addition reaction. Both central chirality and axial chirality have been controlled at the same time using Rh/(R,R)-Ph-bod* catalyst with high enantio- and diastereoselectivity. This method has also been applied to the preparation of a planar-chiral ferrocene derivative. The resulting chiral C-N axis can be used as a good template to control the stereochemistry in the subsequent transformations such as alkylation and Diels-Alder reactions.
- Duan, Wei-Liang,Imazaki, Yusuke,Shintani, Ryo,Hayashi, Tamio
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p. 8529 - 8536
(2008/02/09)
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- ASYMMETRIC-SYNTHESIS CATALYST BASED ON CHIRAL BROENSTED ACID AND METHOD OF ASYMMETRIC SYNTHESIS WITH THE CATALYST
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A compound usable as an asymmetric synthesis catalyst which can be easily synthesized without using any metal such as a lanthanoid group element; a method of asymmetric synthesis with the compound; and a chiral compound obtained by the asymmetric synthesis method. A Broensted acid is used as a catalyst in asymmetric synthesis, the chiral Broensted acid being represented by formula (1) below or formula (3) below. The asymmetric synthesis method employs the catalyst. Asymmetric synthesis with the catalyst gives a chiral compound.
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Page/Page column 20-21
(2010/11/08)
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- Carbon-carbon bond-forming enantioselective synthesis of chiral organosilicon compounds by rhodium/chiral diene-catalyzed asymmetric 1,4-addition reaction
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(Chemical Equation Presented) A new synthetic method for chiral organosilicon compounds through a rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to β-silyl α,β-unsaturated carbonyl compounds has been developed. By employing (R,R)-Bn-bod * as a ligand, a range of arylboronic acids can be coupled with these substrates in very high enantiomeric excess. The resulting β-silyl 1,4-adducts can be converted to β-hydroxy carbonyl compounds or allylsilanes while retaining their stereochemical information.
- Shintani, Ryo,Okamoto, Kazuhiro,Hayashi, Tamio
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p. 4757 - 4759
(2007/10/03)
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- Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides
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Rhodium/chiral diene (S,S)-3b complex has been found to effectively catalyze the 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides, furnishing useful β-chiral Weinreb amides in high enantioselectivity. The Royal Society of Chemistry 2005.
- Shintani, Ryo,Kimura, Takahiro,Hayashi, Tamio
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p. 3213 - 3214
(2007/10/03)
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- Indole derivatives for the treatment of depression and anxiety
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The present invention provides compounds of formula (I): which are useful for treating depression, anxiety, and alleviating the symptoms caused by withdrawal or partial withdrawal from the use of tobacco or of nicotine.
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Page/Page column 77
(2010/02/05)
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- Inhibitors of serotonin reuptake
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This invention provides compounds and a method for the inhibition of serotonin reuptake in mammals.
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- Pyrazine compounds
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A compound of formula (I) wherein R1is selected from the group consisting of phenyl substituted by one or more halogen atoms, naphthyl and naphthyl substituted by one or more halogen atoms; R2is selected from the group consisting of —NH2and —NHC(═O)Ra; R3is selected from the group consisting of —NRbRc, —NHC(═O)Raand hydrogen, R4is selected from the group consisting of hydrogen, -C1-4alkyl, -C1-4alkyl substituted by one or more halogen atoms, —CN, —CH2OH, —CH2ORdand —CH2S(O)xRd; wherein Rarepresents C1-4alkyl or C3-7cycloalkyl, and Rband Rc, which may be the same or different, are selected from hydrogen and C1-4alkyl, or together with the nitrogen atom to which they are attached, form a6-membered nitrogen containing heterocycle, which heterocycle can be further susbtituted with one or more C1-4alkyl; Rdis selected from C1-4alkyl or C1-4alkyl substituted by one or more halogen atoms; x is an integer zero, one or two; and pharmaceutically acceptable derivatives thereof; with the proviso that R1does not represent (a); when R2is —NH2, and both R3and R4are hydrogen.
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- Formal total synthesis of (+)-diepoxin σ
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The highly oxygenated antifungal anticancer natural product (±)-diepoxin σ was prepared in 10 steps and in 15% overall yield from O-methylnaphthazarin. Highlights of the synthetic work include an Ullmann coupling and a possibly biomimetic oxidative spirocyclization for the introduction of the naphthalene ketal as well as the use of a retro-Diels-Alder reaction to unmask the reactive enone moiety in the naphthoquinone bisepoxide ring system. A novel highly bulky chiral binaphthol ligand was developed for a boron-mediated Diels-Alder reaction that constitutes a formal asymmetric total synthesis of (+)-diepoxin σ.
- Wipf, Peter,Jung, Jae-Kyu
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p. 6319 - 6337
(2007/10/03)
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