- Oil-in-water microemulsion: An effective medium for triplet-triplet annihilated upconversion with efficient triplet acceptors
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The oil-in-water (o/w) microemulsion containing bimolecular system of acceptor (9,10-dinaphthylanthracene) and sensitizer (Pd(ii)tetratolylporphyrin), i.e., upconverted o/w microemulsion, was firstly reported for the triplet-triplet annihilated upconversion (TTA-UC) by temperature effects. The correlation between structure/up-conversion performance of three 9,10-dinaphthylanthracenes doped with Pd(ii)tetratolylporphyrin were investigated. Under excitation at an ultralow power density at 60 mW cm-2, the up-converted o/w microemulsion emits green-to-blue upconversion and an efficiency (ΦUC) increase is accompanied by an increase in temperature. The maximum ΦUCvalue for the upconverted o/w microemulsion obtained was as high as 33.12%, which is comparable to its counterpart in a pure organic solvent. Very importantly, there is no need for the upconverted o/w microemulsion to deaerate, which is of critical importance for applications such as upconversion-powered photoelectrochemistry. To the best of our knowledge, the current study represents a simple approach to obtain high TTA-UC without degassing.
- Ye, Changqing,Wang, Bao,Hao, Roukang,Wang, Xiaomei,Ding, Ping,Tao, Xutang,Chen, Zhigang,Liang, Zuoqin,Zhou, Yuyang
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Read Online
- Synthesis and photophysical processes of a novel 1,10-phenanthroline-containing p-conjugated chromophores and Zn(II) chelated complex
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A novel 1,10-phenanthroline-containing p-conjugated chromophore, 3,8-di-(1-naphthyl)-1,10-phenanthroline, was synthesized by Suzuki reaction and its chelated complex was prepared. The UV-visible spectroscopy and photoluminescent (PL) properties were investigated. The results show that when the solution of the complex in THF located in low concentration range (-6 mol/L), the fluorescence emission exhibit only one emission band and the excimer is formed with gradual increase in concentration of the complex. The emission spectra of the complex show obvious solvent effect. In addition, the intermolecular action between the complex and fullerene (C60) were investigated. The fluorescence intensity of the complex is decreased and the maximal emission obvious red-shifted with the increasing of the concentration of C60, which suggests that the strong interactions between the complex and C60 happen in the excited state.
- Zhang, Caihong,Feng, Liheng,Chen, Zhaobin
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Read Online
- Reaction of grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)- aminoborane by a simple hydrolysis
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Diisopropylaminoborane (BH2-N(iPr)2) is prepared by reacting lithium diisopropylaminoborohydride (iPr-LAB) with trimethylsilyl chloride (TMSCl). Aliphatic, aromatic, and heteroaromatic (diisopropylamino) boranes are readily synthesiz
- Bailey, Christopher L.,Murphy, Chris L.,Clary, Jacob W.,Eagon, Scott,Gould, Naomi,Singaram, Bakthan
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Read Online
- Synthesis and functional properties of symmetrically naphthyl-Based oligoarylenes with high glass-transition temperatures
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Symmetrically naphthyl-based π-conjugated oligoarylenes, OPP(4)Ph-TNp, OPP(4)An-TNp and OPP(4)OXTNp have successfully been synthesized by a divergent approach using Pd-catalyzed Suzuki cross-coupling reaction of diiodo- or dibromo-oligoarylene and arylboronic acid as a key step. Their optical, electrochemical and thermal properties have also been characterized. These newly synthesized naphthyl-based oligoarylenes show highly morphological (Tg 149-187 °C) and thermal (Tdec 509-597 °C) stabilities as well as exhibit potential applications in optoelectronic fields.
- Zhang, Xiaolinga,Sun, Kanga,Liu, Yurong,Xiong, Mojunb,Xia, Pingfanga,Li, Zhonghui,Cao, Zijian
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Read Online
- Transmetallations between aryltrialkyltins and borane: Synthesis of arylboronic acids and organotin hydrides
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Aryltrialkyltin compounds react with borane in THF to give mixtures of trialkyltin hydrides and arylboranes, which on hydrolysis give arylboronic acid in high yields. The arylboronic acids are easily separated and obtained free of organotins.
- Faraoni,Koll,Mandolesi,Zú?iga,Podestá
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Read Online
- The synthesis and application of 2-acetyl-6-(1-naphthyl)-pyridine oxime as a new ligand for palladium precatalyst in suzuki coupling reaction
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The synthesis of 2-acetyl-6-(1-naphthyl)-pyridine oxime ligand from 2,6-dibromopyridine and 1-bromo-naphthalene is described, and the new palladium(II) complex used as a Pd(0) precatalyst in the Suzuki cross-coupling reaction was studied. The results showed that the novel naphthalene pyridine oxime complex could serve as an efficient precatalyst.
- Zhou, Yongchang,Kijima, Tatsuro,Izumi, Taeko
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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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- Magnesiation of Aryl Fluorides Catalyzed by a Rhodium-Aluminum Complex
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We report the magnesiation of aryl fluorides catalyzed by an Al-Rh heterobimetallic complex. We show that the complex is highly reactive to cleave the C-F bonds across the polarized Al-Rh bond under mild conditions. The reaction allows the use of an easy-to-handle magnesium powder to generate a range of arylmagnesium reagents from aryl fluorides, which are conventionally inert to such metalation compared with other aryl halides.
- Fujii, Ikuya,Semba, Kazuhiko,Li, Qiao-Zhi,Sakaki, Shigeyoshi,Nakao, Yoshiaki
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supporting information
p. 11647 - 11652
(2020/08/06)
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- Compound taking triarylamine as core, and preparation method and application of compound
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The invention discloses a compound taking triarylamine as a core, and a preparation method and an application of the compound, and belongs to the technical field of semiconductors. The compound provided by the invention has the structure represented by a general formula (1). The invention also discloses the preparation method and the application of the compound. The compound provided by the invention has relatively high glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and relatively high mobility; and the photoelectric property of an OLED devicecan be effectively improved and the service life of the OLED device can be effectively prolonged by optimizing the structure of the device.
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Paragraph 0095-0100
(2020/02/14)
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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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- ROCK inhibitor containing methylnaphthalene and propylene glycol thiophene amide
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The invention belongs to the technical field of medicine. In particular, the invention relates to a compound containing a methylnaphthalene and propylene glycol thiophene amide structure and capable of serving as a ROCK inhibitor, a preparation method thereof and application thereof to preparation of medicines for treating sexual dysfunction, inflammatory diseases, ophthalmic diseases, respiratorysystem diseases and the like. (The formula is as shown in the description).
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Paragraph 0028; 0032; 0033; 0034
(2018/05/16)
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- Compound comprising propanediol thiophene amide and preparation method and application of compound comprising propanediol thiophene amide
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The invention belongs to the technical field of medicines and particularly relates to a compound comprising propanediol thiophene amide, a preparation method of the compound comprising propanediol thiophene amide, and application of the compound comprising propanediol thiophene amide to preparation of medicines for treating sexual dysfunction, inflammatory diseases, eye diseases and diseases of the respiratory system.
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Paragraph 0027; 0028; 0032; 0033; 0034
(2018/07/06)
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- ROCK inhibitor comprising methylnaphthalene and propanediol thiophene amide structure
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The invention belongs to the technical field of medicines and particularly relates to a compound comprising methylnaphthalene and a propanediol thiophene amide structure, a preparation method of the compound, and application of the compound to preparation of medicines for treating sexual dysfunction, inflammatory diseases, eye diseases and diseases of the respiratory system, and the compound can serve as a ROCK inhibitor.
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Paragraph 0027; 0028; 0032; 0033; 0034
(2018/07/06)
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- ROCK inhibitor containing methylnaphthalene and nitrile thiophene amide structures and application
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The invention belongs to the technical field of medicine, in particular to a compound containing methylnaphthalene and nitrile thiophene amide structure, which can serve as a ROCK inhibitor, a preparation method thereof, and application thereof to preparation of medicine for treating sexual dysfunction, inflammatory diseases, ophthalmic diseases and respiratory system diseases.
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Paragraph 0028; 0032; 0033; 0034
(2018/07/30)
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- Alkoxythiophene amide and methylnaphthalene structure containing compounds and preparation method and application thereof
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The invention belongs to the technical field of medicines, and particularly relates to a class of alkoxythiophene amide and methylnaphthalene structure containing compounds, a preparation method thereof and application thereof to preparation of medicines for treating sexual dysfunction, inflammatory diseases, ophthalmic diseases, respiratory system diseases and the like. In a general formula, R isselected from C1-C5 alkyl groups.
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Paragraph 0030; 031; 0035-0036
(2018/07/06)
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- Compound comprising isopropyl naphthalene and propanediol nitrothiophene amide and application of compound
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The invention belongs to the technical field of medicines and particularly relates to a compound comprising isopropyl naphthalene and propanediol nitrothiophene amide, a preparation of the compound comprising isopropyl naphthalene and propanediol nitrothiophene amide, and application of the compound comprising isopropyl naphthalene and propanediol nitrothiophene amide to preparation of medicines for treating medicines for treating sexual dysfunction, inflammatory diseases, eye diseases, and diseases of the respiratory system.
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Paragraph 0024-0025; 0029-0031
(2018/07/06)
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- Propylene glycol thiophene containing amide compounds and preparation method and application thereof
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The invention belongs to the technical field of medicines, and particularly relates to a class of propylene glycol thiophene containing amide compounds, a preparation method thereof and application thereof to preparation of medicines for treating sexual dysfunction, inflammatory diseases, ophthalmic diseases, respiratory system diseases and the like. In a general formula, R is selected from C1-C10alkyl groups and C3-C8 cycloalkyl groups.
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Paragraph 0032; 0033; 0037; 0038; 0039
(2018/07/06)
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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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- Amide compound containing isopropyl naphthalene and propylene glycol thiophene as well as preparation method and application thereof
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The invention belongs to the technical field of pharmaceuticals and particularly relates to an amide compound containing isopropyl naphthalene and propylene glycol thiophene as well as a preparation method and application of the amide compound in preparing a medicine for treating sexual dysfunction, inflammatory diseases, ophthalmic diseases, respiratory system diseases and the like. (The formulais shown in the description), wherein R is selected from alkyl groups of C1 to C5.
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Paragraph 0027; 0028; 0032; 0033; 0034
(2018/08/04)
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- Thiophene amide compounds containing isopropyl naphthalene and propylene glycol and application thereof
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The invention belongs to the field of medical technologies. Specifically, the invention relates to thiophene amide compounds containing isopropyl naphthalene and propylene glycol, a preparation methodthereof and application of the compounds in the preparation of medicines for treating sexual dysfunction, inflammatory diseases, ophthalmic diseases and diseases of the respiratory system. In the formula (I) as shown in the specification, R is selected from F and Cl substituents.
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Paragraph 0025; 0026; 0030-0032
(2018/04/28)
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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 0116-0121
(2017/06/19)
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- Synthesis, photophysical, and electrochemical properties of wide band gap tetraphenylsilane-carbazole derivatives: Effect of the substitution position and naphthalene side chain
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Four tetraphenylsilane-carbazole derivatives with wide bandgaps (3.38–3.55 eV) were synthesized. The effects of the substitution position and of the presence of naphthalene groups on the photophysical, electrochemical and thermal properties were investigated. The derivatives exhibited maximum absorption peaks ranging from 293 to 304 nm and maximum emission peaks ranging from 347 to 386 nm. Changing the carbazole substitution position on the tetraphenylsilane did not significantly change the photophysical and electrochemical properties. However, p-substituted compounds exhibited higher glass transition temperatures than m-substituted compounds. Naphthalene groups with bulky structures had extended the conjugation lengths that red-shifted both the absorption and emission spectra. The LUMO level was decreased, which reduced the optical bandgap and triplet energy level. However, the naphthalene groups significantly improved the thermal stability by increasing the glass transition temperature of the compounds.
- Ho, Kar Wei,Ariffin
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p. 2590 - 2599
(2016/11/18)
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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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- 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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- A novel phenylene typed compound and the organic electroluminescence display device using it
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A phenylene-based compound is provided to ensure excellent blue and green luminescence property and good hole transport property and electron transport property, thereby imparting low voltage, high brightness, and long lifetime. A symmetrical phenylene-based compound has a structure represented by chemical formula 1. In chemical formula 1, Ar1 is substituted or unsubstituted aryl group or substituted or unsubstituted heteroaryl group; and R1, R2, R3, R4 and R5 are independently amino group, nitrile group, nitro group, halogen group, C1~C40 alkyl group, C1~C40 alkoxy group, C3~C40 cycloalkyl group, C3~C40 heterocycloalkyl group, C6~C40 substituted or unsubstituted aryl group or C6~C40 substituted or unsubstituted heteroaryl group.
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Paragraph 0126-0127
(2016/11/21)
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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 0322; 0323; 0324; 0325
(2016/10/10)
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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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- 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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p. 15565 - 15571
(2013/11/19)
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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 0114-0115
(2013/03/26)
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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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supporting information; experimental part
p. 7431 - 7441
(2012/06/16)
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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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- Synthesis of uniformly 13C-labeled polycyclic aromatic hydrocarbons
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Convergent synthetic pathways were devised for efficient synthesis of a series of uniformly 13C labeled polycyclic aromatic hydrocarbons de novo from U-13C-benzene and other simple commercially-available 13C-starting compounds. All target products were obtained in excellent yields, including the alternant PAH U-13C-naphthalene, U-13C-phenanthrene, U-13C-anthracene, U- 13C-benz[a]anthracene, U-13C-pyrene and the nonalternant PAH U-13C-fluoranthene.
- Zhang, Zhenfa,Sangaiah, Ramiah,Gold, Avram,Ball, Louise M.
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p. 5431 - 5435
(2011/09/14)
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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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- Synthesis and photophysical properties of pyrrole/polycyclic aromatic units hybrid fluorophores
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A series of pyrrole/polycyclic aromatic unit hybrid fluorophores was developed by a two-stage synthetic strategy. Their central aryl-substituted pyrrole cores were constructed by a Paal-Knorr pyrrole synthesis reaction. The reaction conditions and mechanism are also discussed in detail. End-capping triflate onto the central pyrrole core enables the core to incorporate various polycyclic aromatic units. The Buchwald-Hartwig amination reaction and the Suzuki-Miyaura cross-coupling reaction were adopted to incorporate the triflate end-capping pyrrole with N-phenylnaphthalen-1-amine and various polycyclic aromatic units to form the hybrid fluorophores. The photophysical properties and thermal properties of the fluorophores were characterized. Most of the pyrrole fluorophores emitted blue light and exhibited high quantum efficiency. The fluorescence properties of these pyrrole fluorophores were induced by manipulating the surrounding polycyclic aromatic units. When the central pyrrole core was incorporated with amino or naphthalene moieties, the fluorescence efficiency and thermal stability of fluorophores 1 and 2 were low (φf g f > 0.99) and stable glassy morphology (the Tg value of the fluorophore 6 was as high as 220 °C). Results of this study demonstrate that the sterically induced fluorescence of crowded pyrrole and the fluorescent polycyclic aromatic units significantly affect the emission properties of the hybrid fluorophores.
- Li, Chang-Shun,Tsai, Ya-Hsuan,Lee, Wei-Chen,Kuo, Wen-Jang
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supporting information; experimental part
p. 4004 - 4013
(2010/08/19)
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- Facile synthesis of spirocyclic aromatic hydrocarbon derivatives based on o-halobiaryl route and domino reaction for deep-blue organic semiconductors
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Conventional o-halobiaryl and one-pot tandem protocols have been developed to synthesize naphthalene- and pyrene-containing spirofluorenes. Two pyrene substituents were installed using a Suzuki cross-coupling reaction to produce a series of spirofluorene-
- Liu, Feng,Xie, Ling-Hai,Tang, Chao,Liang, Jing,Chen, Qing-Quan,Peng, Bo,Wei, Wei,Cao, Yong,Huang, Wei
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supporting information; experimental part
p. 3850 - 3853
(2009/12/06)
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- A general palladium-catalyzed Suzuki-Miyaura coupling of aryl mesylates
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(Chemical Equation Presented) Catalyze this! The first palladium-catalyzed Suzuki-Miyaura coupling of unactivated aryl mesylates is reported, with not only arylboronic acids, but also other organoboron nucleophiles (see picture; Z=B(OH)2, BF3K, BPin). The reaction conditions are compatible with various common functional groups (R1=alkyl, OMe, CHO, CO, CN, CO2R′, heteroaryl).
- So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 8059 - 8063
(2009/04/13)
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- Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts
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A family of indolyl phosphine ligands was applied to Suzuki-Miyaura cross-coupling of aryl tosylates. Catalyst loading can be reduced to 0.2 mol % for coupling of nonactivated aryl tosylate. A challenging example for room temperature coupling is realized. The scope of this highly active Pd/L2 system can be extended to other boron nucleophiles, including trifluoroborate salts and boronate esters. The ligand structural comparisons toward the reactivity in tosylate couplings are also described.
- So, Chau Ming,Lau, Chak Po,Chan, Albert S. C.,Kwong, Fuk Yee
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p. 7731 - 7734
(2008/12/22)
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- Easily accessible and highly tunable Lndolyl phosphine ligands for suzuki-miyaura coupling of aryl chlorides
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This study describes a new class of easily accessible indolyl phosphine ligands, prepared via an efficient protocol involving Fischer indolization from readily available Phenylhydrazine and substituted acetophenones. This versatile ligand scaffold provides beneficial features, including high potential of steric and electronic tunability. The air-stable indolyl phosphines in combination with a palladium metal precursor provide highly effective catalysts for Suzuki-Miyaura coupling of unactivated aryl chlorides, and the catalyst loading down to 0.02 mol % can be achieved.
- So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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p. 2795 - 2798
(2008/02/05)
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- Compositions for oxidatively dyeing keratin fibers and methods for using such compositions
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Compositions for dyeing keratin fibers comprise (a) at least one keratin dyeing compound selected from aromatic systems which comprise at least one boronic acid or boronic ester moiety and which are capable of forming upon oxidation a nucleophile or an electrophile, (b) at least one additional keratin dyeing compound selected from the group consisting of auxiliary developers and auxiliary couplers, and (c) a cosmetically suitable medium. Methods for oxidatively dyeing keratin fibers comprise the steps of applying such compositions in the presence of an oxidizing agent and rinsing the hair. A hair coloring product in kit form comprises a first separately packaged container comprising a composition as described above and a second separately packaged container comprising an oxidizing agent.
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Page/Page column 8
(2008/06/13)
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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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- Methodology for the synthesis of 1,2-disubstituted arylnaphthalenes from α-tetralones
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α-Tetralones were initially converted into 1-bromo- dihydronaphthalene-2-carbaldehydes and 1-bromo-naphthalene-2-carbaldehydes. These precursors were then subjected to Suzuki coupling reactions to afford 1,2-disubstituted aryldihydronaphthalenes and 1,2-disubstituted arylnaphthalenes, respectively. The former products were oxidized with DDQ to give 1,2-disubstituted arylnaphthalenes.
- Moleele, Simon S.,Michael, Joseph P.,De Koning, Charles B.
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p. 2831 - 2844
(2007/10/03)
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- The preparation of a new kind of carbosilane dendrimer with 4-(naphthalen-1-yl)phenyl core - An application of Suzuki coupling reaction
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Using the divergent method, carbosilane dendrimers with p-bromophenyl core were synthesized by using alternating Grignard and hydrosilylation reactions. And then, α-naphthalenyl was connected to the core by using Suzuki coupling reaction. This gave a new carbosilane dendrimer with a 4-(naphthalen-1-yl)phenyl core. All the products were characterized by IR, 1HNMR, 13CNMR, 29SiNMR, and MS. The study shows that Suzuki Coupling reaction is an effective and powerful core- functionalization method and a satisfactory result can be achieved through prolonging the reaction time.
- Zhou, Chuan-Jian,Guan, Rui-Fang,Feng, Sheng-Yu,Berg, David J.,Stobart, Stephen R.
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p. 947 - 952
(2007/10/03)
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- Synthesis of comb-like polyarylenes by oxidattve polymerization of a well-defined polystyrene macromonomer with naphthalene moieties
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Synthesis of a polystyrene (PSt) grafted polyarylene with naphthalene groups in the main chain is described. 1,4-Dibromo-2,5-bis(bromomethyl)benzene was used as initiator in ATRP of styrene using CuBr/2,2′-bipyridine as catalyst and polymeric precursor, that possesses a designed molecular weight with a narrow molecular weight distribution and two bromine atoms directly linked to a central benzene ring, was obtained. The Suzuki coupling between the bromine functionalized PSt and 1-naphihyl boronic acid furnished a macromonomer with naphthyl moieties as oxidable groups. Following chemical oxidative polymerization in the presence of anhydrous FeCl3, a soluble and processable polyarylene with PSt side chains was synthesized. The starting macromonomers as well as the final polyarylenes were analyzed by GPC and spectral methods (1H-NMR, IR and UV-vis). The thermal behaviour of the polymers was studied by differential scanning calorimetry (DSC) and thermogravimetrical analysis (TGA).
- Mercore, Viorela-Mihaela,Cianga, Ioan,Grigoras, Mircea,Yagci, Yusuf
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p. 607 - 616
(2007/10/03)
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- Metallocene compounds, processes for the production of olefin polymers using catalysts containing the compounds, and olefin polymers produced by the processes
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Metallocene compounds represented by the following general formula (1): YqKLMX2??(1) wherein M, Y, q, L and X are each as defined in the Specification.
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Page/Page column 30
(2010/02/07)
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- Thrombopoietin mimetics
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Invented are non-peptide TPO mimetics. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected substituted naphthimidazole derivative.
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- Propanoic acid derivatives
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Propanoic acid derivatives of formula (1) are described: Ar—X1—Ar1—Z—R??(1) in which Ar is a nitrogen base containing group; X1is linker atom or group; Ar1is an optionally substituted 5- or 6-membered nitrogen-containing aromatic or non-aromatic monocycle; Z is a group —CH(R13)CH2— [in which R13is an optionally substituted aliphatic, cycloaliphatic, heteroaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group], —C(R12a)(R13)—CH(R12b)— [in which R12aand R12btogether with the carbon atoms to which they are attached form a C3-7cycloalkyl group] or C(R13)═CH—; R is a carboxylic acid (—CO2H) or a derivative or biostere thereof; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of αVintegrins to their ligands and are of use in the prophylaxis and treatment of immune or inflammatory disorders.
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- Experimental fingerprints of vibrational wave-packet motion during ultrafast heterogeneous electron transfer
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By application of 20 fs laser pulses, vibrational wave packets of low-energy modes (mainly 357 and 421 cm-1) were generated in the perylene chromophore that gave rise to periodic beats that lasted longer than 1 ps in transient absorption signals. Electron transfer from the excited singlet state of the perylene chromophore, attached as molecule DTB-Pe via the -CH2-phosphonic acid group to anatase TiO2, was measured in ultrahigh vacuum with a time constant of 75 fs. The vibrational wave packet that was generated in the donor state continued its motion for several hundred femtoseconds in the product state of the reaction, i.e., in the ionized chromophore. This is direct proof for electron transfer occurring from a nonrelaxed vibrational population that was created by the short laser pulse in the donor molecule. The rise of the product state showed a staircase-like time dependence. The steps are attributed to electron transfer that occurs preferentially each time the vibrational wave packet (frequency 480 cm-1) reaches a crossing point for the potential curves of reactant and product state. Such wave-packet modulation of heterogeneous electron transfer can arise if the density of electronic acceptor states in the electrode is changing strongly over an energy range on the order of the reorganization energy below the excited molecular donor orbital.
- Zimmermann,Willig,Ramakrishna,Burfeindt,Pettinger,Eichberger,Storck
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p. 9245 - 9253
(2007/10/03)
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- Probing the hydrophobic pocket of farnesyltransferase: Aromatic substitution of CAAX peptidomimetics leads to highly potent inhibitors
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Cysteine farnesylation at the carboxylate terminal tetrapeptide CAAX of Ras protein is catalyzed by farnesyltransferase. This lipid modification is necessary for regulatory function of both normal and oncogenic Ras. The high frequency of Ras mutation in human cancers has prompted an intensive study on finding ways of controlling oncogenic Ras function. Inhibition of farnesyltransferase is among the most sought after targets for cancer chemotherapy. We report here the design, synthesis and biological characterization of a series of peptidomimetics as farnesyltransferase inhibitors. These compounds are extremely potent towards farnesyltransferase with IC50 values ranging from subnanomolar to low nanomolar concentrations. They have a high selectivity for farnesyltransferase over the closely related geranylgeranyltransferase-I. Structure-activity relationship studies demonstrated that a properly positioned hydrophobic group significantly enhanced inhibition potency, reflecting an improved complementarity to the large hydrophobic pocket in the CAAX binding site. Copyright (C) 1999 Elsevier Science Ltd.
- Qian, Yimin,Marugan, Juan Jose,Fossum, Renae D.,Vogt, Andreas,Sebti, Said M.,Hamilton, Andrew D.
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p. 3011 - 3024
(2007/10/03)
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