- Synthesis and guest recognition of molecular cleft consisting of terpyridine-Pt(II) acetylide complexes
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The stable molecular clefts 1 consisting of inert Pt-acetylide moieties and a 1,1':30,100-terphenyl spacer were synthesized. Guest binding behavior of 1a was examined by 1H NMR spectroscopy to determine the association constants; naphthalene (Ka0M-1) an
- Nabeshima, Tatsuya,Hasegawa, Yuki,Trokowski, Robert,Yamamura, Masaki
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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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- Cationic platinum(II) complexes bearing aryl-BIAN ligands: Synthesis and structural and optoelectronic characterization
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Five cationic platinum(II) complexes bearing a 2-(3′-substituted aryl)pyridine cyclometalating ligand (C^N) and a neutral Ar-BIAN ligand have been synthesized: [Pt(ppy)(PhBIAN)]PF6 (1), [Pt(3Fppy)(PhBIAN)]PF6 (2), [Pt(3MeOppy)(PhBIAN)]PF6 (3), [Pt(3MeOppy)(4-FPhBIAN)]PF6 (4), [Pt(ppy)(4-MeOPhBIAN)]PF6 (5). All complexes have been characterized by NMR spectroscopy and mass spectrometry. Complexes 2 and 3 have been characterized by X-ray crystallography. Structure-property relationships were established from UV-visible spectroscopy and cyclic voltammetry studies. Interestingly, we found that when both the C^N and the Aryl-BIAN ligands contained electron-donating MeO groups the absorption spectrum for the platinum complex extended out to 650 nm. The electrochemical studies of these complexes established that they are electronically compatible dye molecules for dye-sensitized solar cells.
- Obrien, Cameron,Wong, Michael Yin,Cordes, David B.,Slawin, Alexandra M. Z.,Zysman-Colman, Eli
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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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- Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems
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Asymmetric 1,4-addition reactions with β,γ-unsaturated α-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, β,γ-unsaturated α-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to β,γ-unsaturated α-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal. (Figure presented.).
- Miyamura, Hiroyuki,Yasukawa, Tomohiro,Zhu, Zhiyuan,Kobayashi, Shū
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supporting information
p. 353 - 359
(2019/12/15)
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- An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10
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An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.
- Silva, Renato L.,Santos, Cosme S.,Santos, Jonh A. M.,Oliveira, Roberta A.,Menezes, Paulo H.,Freitas, Juliano C. R.
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p. 1777 - 1785
(2018/09/04)
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- Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors
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This letter presents synthesis and structure-activity relationship study of sulfonamide derivatives as inhibitors of Human Uric Acid Transporter 1 (hURAT1). Among all tested sulfonamide derivatives, compounds 9b, 16i and 19b exhibited excellent inhibition activity with IC50 value of 10, 2, and 83?nM, respectively. In addition, compounds 9b and 19b demonstrated moderate PK profile in rats.
- Yang, Xintuo,Pang, Xuehai,Fan, Lei,Li, Xinghai,Chen, Yuanwei
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supporting information
p. 1919 - 1922
(2017/04/10)
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- Importance of 5/6-aryl substitution on the pharmacological profile of 4?-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1?-biphenyl]-2-carboxylic acid derived PPARγ agonists
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In this structure-activity relationship study, the influence of aryl substituents at position 5 or 6 on the pharmacological profile of the partial PPARγ agonist 4‘-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1‘-biphenyl]-2-carboxylic acid was investigated. This lead was previously identified as the essential part of telmisartan to induce PPARγ activation. Para-OCH3-phenyl substitution strongly increased potency and efficacy independent of the position. Both compounds represent full agonists because of strong hydrophobic contacts with the amino acid Phe363 in the ligand binding domain. Partial agonists with higher potency than telmisartan or the lead were obtained with OH or Cl substituents at the phenyl ring. Molecular modeling suggested additional hydrogen or halogen bonds with Phe360 located at helix 7. It is assumed that these interactions fix helix 7, thereby promoting a partial agonist conformation of the receptor. The theoretical considerations correlate very well with the results from the luciferase transactivation assay using hPPARγ-LBD as well as those from a time-resolved fluorescent resonance energy transfer (TR-FRET) assay in which the coactivator (TRAP220, PGC-1α) recruitment and corepressor (NCoR1) release pattern was investigated.
- Obermoser, Victoria,Mauersberger, Robert,Schuster, Daniela,Czifersky, Monika,Lipova, Marina,Siegl, Monika,Kintscher, Ulrich,Gust, Ronald
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supporting information
p. 590 - 603
(2016/12/09)
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- Boroquinol Complexes with Fused Extended Aromatic Backbones: Synthesis and Optical Properties
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Boron-based dyes are attractive synthetic targets due to their large variability of absorption and emission wavelengths. Through Pictet–Spengler cyclizations, followed by oxidation, π-extended boroquinols have been synthesized. During optimization of the
- Elbert, Sven M.,Wagner, Philippe,Kanagasundaram, Thines,Rominger, Frank,Mastalerz, Michael
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supporting information
p. 935 - 945
(2017/02/05)
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- Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts
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We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.
- Mfuh, Adelphe M.,Doyle, John D.,Chhetri, Bhuwan,Arman, Hadi D.,Larionov, Oleg V.
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supporting information
p. 2985 - 2988
(2016/03/19)
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- Compound containing anthracene and pyrene and preparing method and application thereof
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The invention provides a compound containing anthracene and pyrene and a preparing method and application thereof. The compound has a structure shown in formula I, wherein R1 and R3 are independently selected from substituted or unsubstituted C1-C60 alkyl groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C10-C60 condensed ring groups or substituted or unsubstituted C5-C60 heterocyclic groups; R2 is selected from hydrogen, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C5-C60 heterocyclic groups, substituted or unsubstituted C10-C60 condensed ring groups or substituted or unsubstituted C5-C60 arylamine groups; n is 0 or 1. When current density is 20 mA/cm2, the current efficiency of the compound with the structure shown in formula I is as high as 8.9 cd/A, and service life is as long as 8500 h which is much longer than that of existing electroluminescent materials.
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Paragraph 0147-0152
(2017/02/24)
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- Transition-metal-free synthesis of phenanthridinones from biaryl-2-oxamic acid under radical conditions
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Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products. (Chemical Equation Presented).
- Yuan, Ming,Chen, Li,Wang, Junwei,Chen, Shenjie,Wang, Kongchao,Xue, Yongbo,Yao, Guangmin,Luo, Zengwei,Zhang, Yonghui
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supporting information
p. 346 - 349
(2015/02/19)
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- Stabilised columnar mesophases formed by 1 : 1 mixtures of hexaalkoxytriphenylenes with a hexaphenyltriphenylene-based polymer
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The synthesis is reported for a main chain polymer in which the repeat units are 2,3,6,7,10,11-hexaphenyltriphenylene moieties linked through flexible dodecyl chains. In compositions with a series of 2,3,6,7,10,11-hexakis(alkoxy)triphenylenes (HATn) this
- Mclaren, Sholto R.,Tate, Daniel J.,Lozman, Owen R.,Mehl, Georg H.,Bushby, Richard J.
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p. 5754 - 5763
(2015/06/16)
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- M-Terphenyl-3,3″-dioxo-derived oxacalixaromatics: Synthesis, structure, and solvent encapsulation in the solid state
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The synthesis of oxacalix[2]terphenylene[2]aromatics with enlarged macrocyclic holes by cyclooligomerization reaction of 5′-tert-butyl-(1, 1′:3′,1″-terphenyl)-3,3″-diol 1 with electron-deficient dihalogenated benzene and azaheterocycles is described. The structures of the macrocycles were characterized by NMR, HRMS spectroscopic and X-ray diffraction techniques. Single crystal X-ray analysis revealed that the terphenyl-3, 3″-dioxo unit incorporated in the oxacalix[4]aromatics scaffold can adopt all three possible conformations (I, II, III). The cis-conformational terphenyl-3,3″-dioxo (I and II) derived oxacalix[4]aromatics were found to adopt both chair and boat conformations, resulted in creation of molecular cavities capable of hosting solvent molecules of chloroform. The trans-conformational terphenyl-3,3″-dioxo (III) derived oxacalix[4]aromatics, however, adopt a twisted chair conformation with a narrow void space incapable of hosting any guest molecules.
- Hu, Wen-Jing,Liu, Long-Qing,Ma, Ming-Liang,Zhao, Xiao-Li,Liu, Yahu A.,Mi, Xian-Qiang,Jiang, Biao,Wen, Ke
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supporting information
p. 3934 - 3941
(2013/06/27)
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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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p. 1264 - 1267
(2013/03/14)
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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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- Polymerizable compound and liquid crystal composition including it
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Provided is a polymerizable compound with large solubility in a liquid crystal composition and high reactivity irradiated by ultraviolet in the longer wavelength range. Provided is a liquid crystal composition that satisfies at least one of characteristics such as high maximum temperature of a nematic phase, low minimum temperature of a nematic phase, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light and high stability to heat, or that is suitably balanced between at least two of the characteristics. Provided is the polymerizable compound wherein at least one of a 1,3-phenylene structure and a 2,7-fluorenediyl structure is introduced to the polymerizable compound to give stable displays by forming a polymer with a high degree of polymerization in a PSA device production process using longer wavelengths, the liquid crystal composition includes the compound, and the liquid crystal display device contains the composition.
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Page/Page column 52; 53
(2013/03/27)
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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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- Synthesis and electrochemical properties of peripheral carbazole functional Ter(9,9-spirobifluorene)s
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(Graph Presented) A facile approach for synthesis of spirobifluorene trimers with peripheral carbazole functional groups by utilizing Suzuki coupling as the key reaction has been developed. These novel compounds exhibit blue emission with high quantum yields in solution and thin films, and excellent spectral stability upon photoirradiation and annealing in air. By the introduction of carbazole groups, the oxidation potentials of spirobifluorene trimers STCPC-6 and STCPC-4 were significantly lower than that of model compound STHPH without peripheral carbazole groups, which reflect that the title compounds process higher HOMO energy level and better hole-injection ability. Highly luminescent films were obtained by electrochemical coupling between carbazole units. Pure blue-emission single-layer LEDs based on electrochemical deposition films as light emitting layers were achieved.
- Tang, Shi,Liu, Meirong,Gu, Cheng,Zhao, Yang,Lu, Ping,Lu, Dan,Liu, Linlin,Shen, Fangzhong,Yang, Bing,Yuguang, Ma.
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p. 4212 - 4218
(2008/09/21)
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- Iridium(I)-salicylaldiminato-cyclooctadiene complexes used as catalysts for phenylborylation
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Iridium(I) salicylaldiminato-cyclooctadiene complexes, Ir(-o-O-C6H4-CH{double bond, long}N-R)(cod) (R = CH2Ph (1), Ph (2); cod = 1,5-cyclooctadiene), have been prepared, characterized and used as catalysts for arylborylation via C-H activation. With 1 as a catalyst, isolated yields of up to 91% has been achieved for the borylation of benzene by bis(pinacolato)diboron in the presence of tetra-2-pyridinylpyrazine and an ionic liquid. The catalytic system could be recycled for at least three times without loss of activity.
- Yinghuai, Zhu,Yan, Koh Cheng,Jizhong, Luo,Hwei, Chong Siow,Hon, Yong Chun,Emi,Zhenshun, Su,Winata, Monalisa,Hosmane, Narayan S.,Maguire, John A.
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p. 4244 - 4250
(2008/02/13)
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- Deprotection of pinacolyl boronate esters by transesterification with polystyrene-boronic acid
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A mild, efficient method for the deprotection of pinacolyl organoboronate esters is described. Treatment of the organoboronate ester with excess polystyrene-boronic acid followed by filtration and evaporation of the solvent provides the corresponding organoboronic acid. Mild deprotection of pinacolyl boronate esters to the corresponding boronic acids was achieved in the presence of excess polystyrene-boronic acid via a transesterification process. The procedure allows for the cleavage of pinacolyl boronate esters in the presence of sensitive functional groups. Crown Copyright
- Pennington, Thomas E.,Kardiman, Cynantya,Hutton, Craig A.
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p. 6657 - 6660
(2007/10/03)
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- Benzoxepin-derived estrogen receptor modulators: A novel molecular scaffold for the estrogen receptor
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We present and examine the efficacy of a novel benzoxepin-based scaffold for modulation of the human estrogen receptor. Receptor tolerance of this new molecular scaffold is examined through presentation of experimentally determined antiproliferative effects on human MCF-7 breast tumor cells and measured binding affinities. The effect of functional group substitution on the benzoxepin scaffold is explored through a brief computational structure - activity relationship investigation with molecular simulation.
- Lloyd, David G.,Hughes, Rosario B.,Zisterer, Daniela M.,Williams, D. Clive,Fattorusso, Caterina,Catalanotti, Bruno,Campiani, Giuseppe,Meegan, Mary J.
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p. 5612 - 5615
(2007/10/03)
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- 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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- Indazole compounds, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation
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Indazole compounds that modulate and/or inhibit cell proliferation, such as the activity of protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating, e.g., kinases-dependent diseases to modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.
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- Substituted 2-dialkylaminoalkylbiphenyl derivatives
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Substituted 2-dialkylaminoalkylbiphenyl derivatives, processes for their preparation, pharmaceutical compositions comprising these compounds and methods using these compounds for the preparation of medicaments and for the treatment of diseases.
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- N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
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Thienyl-, furyl- and pyrrolyl-sulfonamides and methods for modulating or altering the activity of the endothelin family of peptides are provided. In particular, N-(isoxazolyl)thienylsulfonamides, N-(isoxazolyl)furylsulfonamides and N-(isoxazolyl)pyrrolylsulfonamides and methods using these sulfonamides for inhibiting the binding of an endothelin peptide to an endothelin receptor by contacting the receptor with the sulfonamide are provided. Methods for treating endothelin-mediated disorders by administering effective amounts of one or more of these sulfonamides or prodrugs thereof that inhibit or increase the activity of endothelin are also provided.
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(2010/01/30)
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- The use of a modified Suzuki reaction for the synthesis of monoarylferrocenes
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A modification of the Suzuki cross-coupling reaction proved to be a clean and useful method for the preparation of monosubstituted arylferrocenes. Iodoferrocene was reacted with a series of substituted arylboronic acids in the presence of sodium carbonate and palladium acetate in aqueous ethanol at room temperature to produce a range of substituted monoarylferrocenes. A systematic investigation undertaken to determine optimal reaction conditions indicated that scrupulous deoxygenation of the solvent is critical. The use of stronger bases such as barium hydroxide and potassium carbonate is favourable and gives rise to better yields of monoarylferrocenes. The reactions also proceed efficiently in aqueous DMF, broadening the scope of the reaction allowing efficient reactions with boronic acids that show low solubility in organic solvents.
- Imrie, Christopher,Loubser, Christa,Engelbrecht, Pieter,McCleland, Cedric W.
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p. 2513 - 2523
(2007/10/03)
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