- Impact of Five-membered Heterocyclic Rings on Photophysical Properties including Two-photon Absorption Character
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A series of dipolar-type terphenyl derivatives 13 featuring an electron donor (p-NMe2C6H4 group) and acceptor (p-NO2C6H4 group) unit was synthesized and their photophysical properties were
- Abe, Manabu,Chitose, Youhei,Lin, Tzu-Chau,Pham, Thuy Thi Thu,Tam, Tran Thi Thanh,Tseng, Wei-Lun
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supporting information
p. 1810 - 1813
(2021/10/27)
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- Immobilization of Ir(I) complex on covalent triazine frameworks for C–H borylation reactions: A combined experimental and computational study
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Metal-modified covalent triazine frameworks (CTFs) have attracted considerable attention in heterogeneous catalysis due to their strong nitrogen-metal interactions exhibiting superior activity, stability and hence recyclability. Herein, we report on a post-metalation of a bipyridine-based CTFs with an Ir(I) complex for C–H borylation of aromatic compounds. Physical characterization of the Ir(I)-based bipyCTF catalyst in combination with density functional theory (DFT) calculations exhibit a high stabilization energy of the Ir-bipy moiety in the frameworks in the presence of B2Pin2. By using B2Pin2 as a boron source, Ir(I)@bipyCTF efficiently catalyzed the C–H borylation of various aromatic compounds with excellent activity and good recyclability. In addition, XAS analysis of the Ir(I)@bipyCTF gave clear evidence for the coordination environment of the Ir.
- Tahir, Norini,Muniz-Miranda, Francesco,Everaert, Jonas,Tack, Pieter,Heugebaert, Thomas,Leus, Karen,Vincze, Laszlo,Stevens, Christian V.,Van Speybroeck, Veronique,Van Der Voort, Pascal
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p. 135 - 143
(2019/02/12)
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- Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
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An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.
- Hoque, Md Emdadul,Bisht, Ranjana,Haldar, Chabush,Chattopadhyay, Buddhadeb
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supporting information
p. 7745 - 7748
(2017/06/21)
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- ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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The present invention relates to a novel compound having excellent light-emitting ability and hole transporting ability, and relates to an organic electroluminescent device comprising the same in at least one organic matter layer, thereby having improved
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Paragraph 0123-0124; 0144-0147
(2016/10/27)
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- Iridium-catalyzed C-H borylation of heterocycles using an overlooked 1,10-phenanthroline ligand: Reinventing the catalytic activity by understanding the solvent-assisted neutral to cationic switch
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The preformed catalyst [Ir(Cl)(COD)(1,10-phenanthroline)] (2; COD = cyclooctadiene) was found to be highly effective in a model reaction for the borylation of N-Boc-indole at the 3-position with B2pin2 (pin = pinacolato) as the borylating agent to give consistently 99% yield with 0.5 mol % catalyst loading. The corresponding in situ formed catalyst from [Ir(Cl)(COD)]2 and 1,10-phenanthroline provided very inconsistent results for the same reaction (0-94% conversion). We propose this to be due to the competing formation of a catalytically inactive cationic complex, [Ir(COD)(1,10-phenanthroline)]+Cl- (1), in a noncoordinating solvent such as octane. Complexes 1 and 2 were characterized using solid-state NMR (13C and 35Cl) in conjunction with XPS to be cationic and neutral, respectively. The X-ray crystal structure of a pentavalent neutral Ir complex, [Ir(Cl)(COD)(2,2′-bipyridine)] (3), was also obtained for comparison purposes. Using catalyst 2, the total synthesis of Meridianin G was accomplished in 87% overall isolated yield in a one-pot, three-step process.
- Seechurn, Carin C. C. Johansson,Sivakumar, Vilvanathan,Satoskar, Deepak,Colacot, Thomas J.
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p. 3514 - 3522
(2014/08/05)
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- Catalytic borylation of o-xylene and heteroarenes via C-H activation
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Iridium and rhodium complexes catalyze the borylation of xylene and different heteroarenes using pinacolborane via C-H activation. Various five-membered heterocycles such as thiophene, pyrrole, thionaphthene, and indole derivatives yield the borylated pro
- Mertins, Kristin,Zapf, Alexander,Beller, Matthias
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- PROCESS FOR PRODUCTION OF HETEROARYL-TYPE BORON COMPOUNDS WITH IRIDIUM CATALYST
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The present invention provides an economically and industrially superior simple process that enables the selective production of an aromatic heterocyclic monoboron compound and aromatic heterocyclic diboron compound at a satisfactory yield and in a desired ratio by reacting an aromatic heterocyclic compound and a boron compound in a single step under mild conditions while changing only the charged ratios of the raw materials. The present invention provides a production process of a heteroaryl mono- or diboron compound comprising an aromatic heterocyclic compound and a boron compound in the form of bis(pinacolate)diboron or pinacolate diborane in the presence of a iridium-containing catalyst and a ligand such as a bipyridyl ligand.
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- Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: Regioselective synthesis of heteroarylboronates
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The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80-100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromatics was also achieved by using an almost equimolar amount of substrates and the diboron.
- Takagi, Jun,Sato, Kazuaki,Hartwig, John F,Ishiyama, Tatsuo,Miyaura, Norio
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p. 5649 - 5651
(2007/10/03)
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