- Synthesis and luminescence properties of two Ir(iii) complexes containing styrene-modified phenylpyridine ligands
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Two new green-emitting iridium(iii) complexes containing styrene-modified phenylpyridine ligands, namely, Ir(ppy-VB)2(acac) (Ir-A) and Ir(ppy-VB)2(Stpip) (Ir-S), where ppy-VB = 2-(4-(((4-vinylbenzyl)oxy)methyl)phenyl)pyridine, acac =
- Wu, Shaoguang,Wang, Youjia,Zhao, Yuling,Wang, Ruidong,Hailin, Ma,Yu, Tianzhi
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p. 3311 - 3318
(2021/02/26)
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- PYRROLIDINE GLYCOSIDASE INHIBITORS
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Compounds of formula (I) wherein A, W, R3b, Z and p have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.
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- UV Light Generation and Challenging Photoreactions Enabled by Upconversion in Water
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Sensitized triplet-triplet annihilation (sTTA) is the most promising mechanism for pooling the energy of two visible photons, but its applications in solution were so far limited to organic solvents, with a current maximum of the excited-singlet state energy of 3.6 eV. By combining tailor-made iridium complexes with naphthalenes, we demonstrate blue-light driven upconversion in water with unprecedented singlet-state energies approaching 4 eV. The annihilators have outstanding excited-state reactivities enabling challenging photoreductions driven by sTTA. Specifically, we found that an aryl-bromide bond activation can be achieved with blue photons, and we obtained full conversion for the very energy-demanding decomposition of a persistent ammonium compound as typical water pollutant, not only with a cw laser but also with an LED light source. These results provide the first proof-of-concept for the usage of low-power light sources for challenging reactions employing blue-to-UV upconversion in water and pave the way for the further development of sustainable light-harvesting applications.
- Pfund, Bj?rn,Steffen, Debora M.,Schreier, Mirjam R.,Bertrams, Maria-Sophie,Ye, Chen,B?rjesson, Karl,Wenger, Oliver S.,Kerzig, Christoph
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p. 10468 - 10476
(2020/07/27)
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- Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation
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An efficient and direct ruthenium-catalyzed regioselective hydroxymethylation of (hetero)arenes via C-H activation with paraformaldehyde as a hydroxymethylating reagent is described. The corresponding products can be obtained in good to excellent yield. A number of aryl aldehydes can also be used in place of paraformaldehyde giving the desired alcohol products with similarly good results.
- Zhang, Guo-Fu,Li, Yue,Xie, Xiao-Qiang,Ding, Cheng-Rong
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supporting information
p. 1216 - 1219
(2017/03/14)
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- Biaryl pyridine palladacycles nitrogen heterocyclic carbene compound and its preparation and use
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The invention discloses an aryl-pyridine cyclic Pd-N heterocyclic carbene compound. The general formula of the compound is described in the specification, wherein X is selected from Cl, Br and I, L is an N-heterocyclic carbene ligand, and Aryl is an aryl. The invention also discloses a preparation method of the compound. The preparation method comprises the following steps of: adding 2-(4-halogen atom phenyl)-pyridine, imidazolium salt, arylboronic acid, halogenated palladium and alkaline into an organic solvent, heating under the protection of gas, filtering after reaction is finished, drying by distillation, and purifying, thus the aryl-pyridine cyclic Pd-N heterocyclic carbene compound is obtained. The compound can serve as a catalyst and is used for catalyzing reaction between halogenated benzyl alcohol and arylboronic acid to synthesize aryl methyl alcohol. The preparation method has the characteristics of various substrates, mild reaction conditions, high yield, economy and high efficiency and has an important practical value.
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Paragraph 0063; 0064
(2017/01/31)
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- Water-soluble palladacycles containing hydroxymethyl groups: Synthesis, crystal structures and use as catalysts for amination and Suzuki coupling of reactions
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Two water-soluble monophosphine [PPh3 and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl(Sphos)]-palladacycles containing hydroxymethyl groups 2-3 were prepared by cyclopalladation and chloride bridge-splitting reactions. The complexes were characterized by elemental analysis, ESI-MS and NMR. In addition, single-crystal X-ray analysis reveals that they have one-dimensional lamellar structures involving intermolecular hydrogen bonds and π-π interactions. The use of these palladacycles as catalysts for amination and Suzuki coupling of aryl chlorides in water was investigated. Complex 3 was found to be very efficient for these coupling reactions. Additionally, it was also successfully used in Suzuki coupling of (hydroxymethyl)phenylboronic acid for the synthesis of substituted 2-N-heterocyclic biarylmethanols.
- Han, Xin,Li, Hong-Mei,Xu, Chen,Xiao, Zhi-Qiang,Wang, Zhi-Qiang,Fu, Wei-Jun,Hao, Xin-Qi,Song, Mao-Ping
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p. 403 - 411
(2016/04/19)
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- Contrasting Anticancer Activity of Half-Sandwich Iridium(III) Complexes Bearing Functionally Diverse 2-Phenylpyridine Ligands
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We report the synthesis, characterization, and antiproliferative activity of 15 iridium(III) half-sandwich complexes of the type [(η5-Cp?)Ir(2-(R′-phenyl)-R-pyridine)Cl] bearing either an electron-donating (-OH, -CH2OH, -CH3) or electron-withdrawing (-F, -CHO, -NO2) group at various positions on the 2-phenylpyridine (2-PhPy) chelating ligand giving rise to six sets of structural isomers. The X-ray crystal structures of [(η5-Cp?)Ir(2-(2′-fluorophenyl)pyridine)Cl] (1) and [(η5-Cp?)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) exhibit the expected "piano-stool" configuration. DFT calculations showed that substituents caused only localized effects on the electrostatic potential surface of the chelating 2-PhPy ligand of the complexes. Hydrolysis of all complexes is rapid, but readily reversed by addition of NaCl. The complexes show preferential binding to 9-ethylguanine over 9-methyladenine and are active catalysts for the oxidation of NADH to NAD+. Antiproliferative activity experiments in A2780 ovarian, MCF-7 breast, A549 lung, and HCT116 colon cancer cell lines showed IC50 values ranging from 1 to 89 μM, with the most potent complex, [(η5-Cp?)Ir(2-(2′-methylphenyl)pyridine)Cl] (13) (A2780 IC50 = 1.18 μM), being 10× more active than the parent, [(η5-Cp?)Ir(2-phenylpyridine)Cl], and 2× more active than [(η5-CpxPh)Ir(2-phenylpyridine)Cl]. Intriguingly, contrasting biological activities are observed between structural isomers despite exhibiting similar chemical reactivity. For pairs of structural isomers both the nature and position of the functional group can affect the hydrophobicity of the complex. An increase in hydrophobicity resulted in enhanced cellular-iridium accumulation in A2780 ovarian cells, which generally gave rise to an increase in potency. The structural isomers [(η5-Cp?)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) and [(η5-Cp?)Ir(2-phenyl-5-fluoropyridine)Cl] (4) preferentially localized in the cytosol > membrane and particulate > nucleus > cytoskeleton. This work highlights the strong dependence of biological behavior on the nature and position of the substituent on the chelating ligand and shows how this class of organometallic anticancer complexes can be fine-tuned to increase their potency without using extended cyclopentadienyl systems. (Chemical Equation Presented).
- Millett, Adam J.,Habtemariam, Abraha,Romero-Canelón, Isolda,Clarkson, Guy J.,Sadler, Peter J.
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supporting information
p. 2683 - 2694
(2015/06/23)
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- N -substituted hydroxylamines as synthetically versatile amino sources in the iridium-catalyzed mild C-H amidation reaction
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N-Substituted hydroxylamines such as aroyloxy- or acyloxycarbamates were successfully employed as synthetically versatile amino precursors in the iridium-catalyzed direct C-H amidation of arenes. The reaction proceeds smoothly at room temperature over a broad range of substrates with high functional group tolerance to afford N-substituted arylamine products.
- Patel, Pitambar,Chang, Sukbok
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supporting information
p. 3328 - 3331
(2014/07/08)
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- Nanostructured RuO2 on MWCNTs: Efficient catalyst for transfer hydrogenation of carbonyl compounds and aerial oxidation of alcohols
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Multiwall carbon nanotubes (MWCNTs)/ruthenium dioxide nanoparticles (RuO2NPs) composite was prepared by a straightforward 'dry synthesis' method. After being well characterized, the prepared composite was used as a nanocatalyst (RuO2/MWCNT) for the transfer hydrogenation of carbonyl compounds. The excellent adhesion of RuO2NPs on the anchoring sites of MWCNTs was confirmed by TEM and Raman analyses. The weight percentage (7.97 wt%) and the chemical state (+4) of Ru in RuO2/MWCNT was confirmed by EDS and XPS analyses, respectively. It was found that the RuO2/MWCNT has a higher specific surface area of 189.3 m2 g-1. Initially the reaction conditions were optimized and then the scope of the catalytic system was extended with a wide range of carbonyl compounds. The influence of the size of RuO2NPs on the transfer hydrogenation of carbonyl compounds was also studied. The RuO2/MWCNT is highly chemoselective, heterogeneous in nature, reusable and highly stable. Owing to the high stability of the used catalyst (u-RuO2/MWCNT), it was further calcinated at high temperature to obtain RuO2 nanorods (NRs) hybrid MWCNTs. Then the hybrid material was used as a catalyst (r-RuO 2/MWCNT) for the aerial oxidation of alcohols and the result was found to be good.
- Gopiraman,Babu, S. Ganesh,Karvembu,Kim
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- Synthesis and properties of a dendritic FRET donor-acceptor system with cationic iridium(iii) complex core and carbazolyl periphery
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In order to enhance the photoluminescence of cyclometalated iridium(iii) complexes, which are potentially useful for biolabeling and bioimaging, a series of benzyl ether branched dendritic moieties with carbazolyl termini were introduced to the cyclometal
- Li, Yanfang,Liu, Yang,Zhou, Ming
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p. 2582 - 2591
(2012/05/04)
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- Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation
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We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N2 as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.
- Kim, Ji Young,Park, Sae Hume,Ryu, Jaeyune,Cho, Seung Hwan,Kim, Seok Hwan,Chang, Sukbok
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supporting information; experimental part
p. 9110 - 9113
(2012/07/14)
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- Bioconversion of aromatic compounds by Escherichia coli that expresses cytochrome P450 CYP153A13a gene isolated from an alkane-assimilating marine bacterium Alcanivorax borkumensis
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The cytochrome P450 CYP153 family has been isolated from alkane-assimilating bacteria. CYP153 has been shown to mediate terminal hydroxylations of linear alkanes or alkyl aromatics. We here performed the biotransformation of various aromatic compounds by Escherichia coli cells that expressed the CYP153A13a (P450balk) gene, which was isolated from an alkane-degading marine bacterium Alcanivorax borkumensis. Aromatic compounds including a short alkyl moiety or methyl ether moiety, and phenolic compounds were converted to their respective hydroxylated products, whose structures were determined by HRMS and NMR analyses. The present study revealed that the catalytic function of CYP153A13a is multifunctional, i.e., it can hydroxylate not only the terminal of short alkyl groups that attached to aromatic rings but also the p-position of phenolic compounds substituted with a halogen or the acetyl group. CYP153A13a was also shown to demethylate methylether-including aromatic compounds.
- Otomatsu, Toshihiko,Bai, Liming,Fujita, Naoya,Shindo, Kazutoshi,Shimizu, Keiko,Misawa, Norihiko
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experimental part
p. 234 - 240
(2011/01/03)
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- Calix[6]arene derivatives selectively functionalized at alternate sites on the smaller rim with 2-phenylpyridine and 2-fluorenylpyridine substituents to provide deep cavities
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The synthesis is described of calix[6]arene derivatives 4, 9, and 14 functionalized at alternate sites on the smaller rim with 4′-(pyrid- 2″-yl)phenylmethoxy, (6′-phenylpyrid-3′-ylmethoxy), and {6′-[2-(9,9-di-n-hexylfluorenyl)]pyrid-3′-ylmethoxy} substitu
- Zeng, Xianshun,Batsanov, Andrei S.,Bryce, Martin R.
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p. 9589 - 9594
(2007/10/03)
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- Compositions and methods of treating cell proliferation disorders
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The invention relates to compounds and methods for treating cell proliferation disorders.
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Page/Page column 76
(2008/06/13)
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- Phosphorescent side-chain functionalized poly(norbornene)s containing iridium complexes
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Norbornenes containing phosphorescent iridium complexes based on Ir(ppy)3 and Ir(ppy)2-(bpy)(PF6) were synthesized and copolymerized with alkylnorbornenes via ring-opening metathesis polymerization in nonpolar solvents usi
- Carlise, Joseph R.,Wang, Xian-Yong,Weck, Marcus
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p. 9000 - 9008
(2008/02/01)
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- Inhibitors of farnesyl-protein transferase
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The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invent
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- Photo-Arylation. IV. Synthesis of 2-Arylpyridines by Photo-Reaction of 2-Iodopyridine with Substituted Benzenes
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Photolysis of a mixture of 2-iodopyridine and a variety of substituted benzenes in dichloromethane afforded the corresponding 2-arylpyridines as isomeric mixtures.Based on the isomer distributions of the products and the formation of 2-chloropyridine as a by-product, the reactivity of 2-iodopyridine in the present reaction was suggested to be electrophilic in character.Keywords - arylpyridine; 2-pyridinylation; photo-arylation; photolysis; 2-iodopyridine; homolytic aromatic substitution
- Terashima, Masanao,Seki, Koh-ichi,Yoshida, Chihiro,Ohkura, Kazue,Kanaoka, Yuichi
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p. 1009 - 1015
(2007/10/02)
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