- Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions
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We report a metal-organic framework (MOF) supported monoligated phosphine-cobalt complex, which is an active heterogeneous catalyst for aromatic C?H borylation and alkene hydroboration. The mono(phosphine)-Co catalyst (MOF?P?Co) was prepared by metalation of a porous triarylphosphine-functionalized MOF (MOF?P) with CoCl2 followed by activation with NaEt3BH. The MOF catalyst has a broad substrate scope with excellent functional group tolerance to afford arene- and alkyl-boronate esters in excellent yields and selectivity. MOF?P?Co gave a turnover number (TON) of 30,000 and could be recycled and reused at least 13 times in arene C?H borylation. Importantly, the attempt to prepare the homogeneous control (Ph3P?Co) using triphenylphosphine was unsuccessful due to the facile disproportionation reactions or intermolecular ligand exchanges in the solution. In contrast, the site isolation of the active mono(phosphine)-Co species within the MOF affords the robust and coordinatively unsaturated metal complexes, allowing to explore their catalytic properties and the reaction mechanism.
- Akhtar, Naved,Antil, Neha,Balendra,Begum, Wahida,Chauhan, Manav,Gupta, Poorvi,Kumar, Ajay,Malik, Jaideep,Manna, Kuntal,Newar, Rajashree
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supporting information
(2022/03/15)
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- Arene borylation through C–H activation using Cu3(BTC)2 as heterogeneous catalyst
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C–H borylation by diborane is an important process to access organoboron compounds. Noble metals, including Ir and Rh-based complexes either in the form of homogeneous or heterogeneous catalysts, have been reported to promote arene C–H borylation. Recently, metal organic frameworks (MOFs) having Ir and Co as active sites have been used as catalysts, but they require co-catalysts. In the present study, commercially available Cu3(BTC)2 (BTC: 1,3,5-benzenetricarboxylate) MOF is reported as an effective catalyst to promote borylation of arenes through C–H activation employing bis(pinacolato)diboron (1) as reagent leading to benzylic and aromatic borylation products. Interestingly, other related MOFs like MIL-101(Cr) and Al(OH)(BDC) (BDC: 1,4-benzenedicarboxylate) do not exhibit catalytic activity under identical conditions. Mechanistic studies using in-situ IR spectroscopy reveal that Cu ions play a crucial role in activating the arene and B–B bond in 1.
- Dhakshinamoorthy, Amarajothi,García, Cristina Vallés,Concepcion, Patricia,Garcia, Hermenegildo
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p. 212 - 217
(2020/07/06)
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- Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides
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Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.
- Cao, Jilei,Tang, Xinxin,Toh, Ren Wei,Wang, Han,Wu, Jie,Wu, Xiangyang,Xu, Jinhui,Yang, Xiaona,Yeow, Edwin K. L.,Zhou, Rong
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supporting information
p. 13266 - 13273
(2021/09/07)
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- Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates
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Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.
- Cai, Mingzhong,Huang, Bin,Luo, Chengkai,Xu, Caifeng
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- Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes
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A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.
- Tian, Ya-Ming,Guo, Xiao-Ning,Krummenacher, Ivo,Wu, Zhu,Nitsch, J?rn,Braunschweig, Holger,Radius, Udo,Marder, Todd B.
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supporting information
p. 18231 - 18242
(2020/11/02)
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- Single-Site Cobalt-Catalyst Ligated with Pyridylimine-Functionalized Metal-Organic Frameworks for Arene and Benzylic Borylation
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We report a highly active single-site heterogeneous cobalt-catalyst based on a porous and robust pyridylimine-functionalized metal-organic frameworks (pyrim-MOF) for chemoselective borylation of arene and benzylic C-H bonds. The pyrim-MOF having UiO-68 topology, constructed from zirconium-cluster secondary building units and pyridylimine-functionalized dicarboxylate bridging linkers, was metalated with CoCl2 followed by treatment of NaEt3BH to give the cobalt-functionalized MOF-catalyst (pyrim-MOF-Co). Pyrim-MOF-Co has a broad substrate scope, allowing the C-H borylation of halogen-, alkoxy-, alkyl-substituted arenes as well as heterocyclic ring systems using B2pin2 or HBpin (pin = pinacolate) as the borylating agent to afford the corresponding arene- or alkyl-boronate esters in good yields. Pyrim-MOF-Co gave a turnover number (TON) of up to 2500 and could be recycled and reused at least 9 times. Pyrim-MOF-Co was also significantly more robust and active than its homogeneous control, highlighting the beneficial effect of active-site isolation within the MOF framework that prevents intermolecular decomposition. The experimental and computational studies suggested (pyrim?-)CoI(THF) as the active catalytic species within the MOF, which undergoes a mechanistic pathway of oxidative addition, turnover limiting σ-bond metathesis, followed by reductive elimination to afford the boronate ester.
- Akhtar, Naved,Antil, Neha,Balendra,Begum, Wahida,Kumar, Ajay,Manna, Kuntal,Newar, Rajashree,Shukla, Sakshi
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supporting information
p. 10473 - 10481
(2020/08/05)
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- Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes
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Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.
- Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Golenko, Yulia D.,Gribanov, Pavel S.,Sterligov, Grigorii K.,Kirilenko, Nikita Yu.,Ageshina, Alexandra A.,Bermeshev, Maxim V.,Nechaev, Mikhail S.,Asachenko, Andrey F.
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p. 569 - 571
(2020/10/09)
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- Iridium-Catalyzed sp3 C-H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands
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Iridium-catalyzed alkane C-H borylation has long suffered from poor atom economy, resulting from both the inclusion of only 1 equiv of boron from the diboron reagent and a requirement for neat substrate. An appropriately substituted dipyridylarylmethane ligand was found to give highly active alkane borylation catalysts that facilitate C-H borylation with improved efficiency. This system provides for complete consumption of the diboron reagent, producing 2 molar equivalents of product at low catalyst loadings. The superior efficacy of this system also enables borylation of unactivated alkanes in hydrocarbon solvent with a reduced excess of substrate and improved functional group compatibility. The effectiveness of this ligand is displayed across a selection of functional groups, both under traditional borylation conditions in neat substrate and under atypical conditions in cyclohexane solvent. The utility of this catalytic system is exemplified by the borylation of substrates containing polar functionality, which are unreactive toward C-H borylation under neat conditions.
- Jones, Margaret R.,Fast, Caleb D.,Schley, Nathan D.
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p. 6488 - 6492
(2020/04/30)
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- Expanding the Variety of Zirconium-based Inorganic Building Units for Metal–Organic Frameworks
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Two new zirconium-based metal–organic frameworks with the composition [Zr6O4(OH)4(OAc)6(BDC)3] (CAU-26) and [Zr5O4(OH)4(OAc)4(BDC)2] (CAU-27) are
- Leubner, Sebastian,Zhao, Haishuang,Van Velthoven, Niels,Henrion, Micka?l,Reinsch, Helge,De Vos, Dirk E.,Kolb, Ute,Stock, Norbert
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supporting information
p. 10995 - 11000
(2019/07/12)
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- Synthesis of Amino- and Hydroxymethyl Benzoxaboroles: Prominent Scaffolds for Further Functionalization
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Herein, we describe the development of a short, simple, and efficient synthesis of amino- and hydroxymethyl-substituted benzoxaboroles. The key step in our strategy was the early stage incorporation of the boron by the borylation of an aniline. The formed boronates were then elaborated to the final products in two additional steps, usually in good yields. The synthetic sequence was amenable to be performed on a preparative scale and 4-amino benzoxaborole 4b and 6-hydroxymethyl benzoxaborole 10c have been prepared, without any significant decrease in the overall yield. The amino and hydroxymethyl present at the molecules are useful for further elaboration and/or conjugation to bioactive molecules and therefore we believe that this method should be useful in the development of new compounds for Medicinal Chemistry.
- Fuscaldo, Rodrigo S.,Vontobel, Pedro H. V.,Boeira, Eduam O.,Moro, Angélica V.,Costa, Jessie S. da
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p. 2050 - 2055
(2019/03/07)
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- Nickel-Catalyzed C(sp2)-H Borylation of Arenes
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In this study, C(sp2)-H borylation of arenes was accomplished by a nickel catalyst, resulting in good yield. Alkyl and alkoxy arenes were successfully functionalized, affording C(sp2)-H borylated compounds. It was unraveled that the well-defined abnormal N-heterocyclic carbene based Ni(II) complex breaks into Ni nanoparticles (Ni-NPs), which act as catalytically active species. A series of controlled reactions under stoichiometric conditions along with spectroscopic studies and single-crystal X-ray crystallographic study helped us to understand the formation of Ni-NPs along with formation of a boron(III) compound during this reaction.
- Das, Arpan,Hota, Pradip Kumar,Mandal, Swadhin K.
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- C-H borylation by platinum catalysis
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Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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p. 332 - 342
(2017/05/09)
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- Benzocarbazoles dioxane derivatives, its preparation process and its use in medicine
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The invention relates to a benzodioxane derivative, a preparation method thereof and application of the derivative in medicines. Specifically, the invention relates to a novel benzodioxane derivative shown as a formula (I), medial salt thereof or a medicine composition containing the derivative, and a preparation method of the derivative. The invention further relates to a use of the benzodioxane derivative and the medial salt thereof or the medicine composition containing the derivative in preparing therapeutic agent, especially GPR 40 agonist, and a drug for treating the diseases such as diabetes, metabolic disorders and the like, wherein each substituent group in the formula (I) is as defined in the description.
- -
-
Paragraph 0391; 0393-0396
(2016/10/10)
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- C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
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Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 12211 - 12214
(2015/10/12)
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- B-H bond cleavage via metal-ligand cooperation by dearomatized ruthenium pincer complexes
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Organic derivatives of boronic acid are widely used reagents useful in various synthetic applications. A fundamental understanding and the exploration of new reaction pathways of boronic reagents with organometallic systems hold promise for useful advancement in chemical catalysis. Herein we present the reactions of simple boranes with dearomatized ruthenium pincer complexes based on PNP (2,6-bis(di-tert-butylphosphinomethyl)pyridine) or PNN (2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine) ligands. NMR studies revealed dehydrogenative addition of the borane B-H bond across the metal center and the ligand. Remarkably, new complexes were observed, which contain the boryl moiety at the benzylic carbon of the pincer ligand arm. X-ray crystal structures of new dearomatized boryl pincer complexes were obtained, and DFT calculations revealed mechanistic details of the adduct formation process through a dehydrogenative pathway. In addition, catalytic aryl-boron coupling reactions were explored. The new boryl pincer systems may possibly be useful in future postmodification techniques for ruthenium pincer complexes, as well as in catalytic B-B and B-C coupling reactions.
- Anaby, Aviel,Butschke, Burkhard,Ben-David, Yehoshoa,Shimon, Linda J. W.,Leitus, Gregory,Feller, Moran,Milstein, David
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supporting information
p. 3716 - 3726
(2014/08/18)
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- Base metal catalysts for photochemical C-H borylation that utilize metal-metal cooperativity
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Heterobimetallic Cu-Fe and Zn-Fe complexes catalyze C-H borylation, a transformation that previously required noble metal catalysts. The optimal catalyst, (IPr)Cu-FeCp(CO)2, exhibits efficient activity at 5 mol% loading under photochemical conditions, shows only minimal decrease in activity upon reuse, and is able to catalyze borylation of a variety of arene substrates. Stoichiometric reactivity studies are consistent with a proposed mechanism that exploits metal-metal cooperativity and showcases bimetallic versions of the classical organometallic processes, oxidative addition and reductive elimination.
- Mazzacano, Thomas J.,Mankad, Neal P.
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supporting information
p. 17258 - 17261
(2014/01/06)
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- Nano-Fe2O3-catalyzed direct borylation of arenes
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Nano-Fe2O3-catalyzed borylation of arenes with diboron pinacol ester B2pin2 has been found to give borylation products with selectivity controlled by electronic effects of substituents. The Royal Society of Chem
- Yan, Guobing,Jiang, Yubo,Kuang, Chunxiang,Wang, Shuai,Liu, Haichao,Zhang, Yan,Wang, Jianbo
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p. 3170 - 3172
(2010/08/06)
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- Microwave-accelerated iridium-catalyzed borylation of aromatic C-H bonds
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Image Persented Microwave heating accelerates the Ir-catalyzed C-H borylation of aromatic substrates when compared with reactions carried out at the same temperature under standard heating conditions. Application to a one-pot single solvent process for ta
- Harrisson, Peter,Morris, James,Marder, Todd B.,Steel, Patrick G.
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supporting information; experimental part
p. 3586 - 3589
(2011/02/22)
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- Iridium complexes of N-heterocyclic carbenes in C-H borylation using energy efficient microwave technology: Influence of structure, ligand donor strength and counter ion on catalytic activity
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Bridged and unbridged N-heterocyclic carbene (NHC) ligands were metalated with [Ir(COD)Cl]2 to give iridium(i) mono- and biscarbene substituted catalysts [Ir(COD)NHC(Cl)] and [Ir(COD)(NHC)2][X] (X: I, PF 6, BF4, CF3COO, OTf). The prepared NHC-complexes were tested in the C-H borylation reaction of aromatic carbons with bis(pinacolato)diboron (B2pin2) and pinacolborane (HBpin). The use of microwave technology in this study not only facilitates a time efficient screening of a wide range of influences such as ligand σ-donor strength and structural motif as well as the effects of the complex counter ion, but also provides an energy efficient heating source. Catalyst 6TFA, which features a chelating NHC ligand, proved to be most effective catalyst and further investigations with this complex in the borylation of mono- and disubstituted benzene derivatives exploring chemo- and regioselectivity were undertaken. The Royal Society of Chemistry 2009.
- Rentzsch, Christoph F.,Tosh, Evangeline,Herrmann, Wolfgang A.,Kuehn, Fritz E.
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scheme or table
p. 1610 - 1617
(2010/05/18)
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- An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane
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(Chemical Equation Presented) borylation of aryl halides with an inexpensive and atom-economical boron source, pinacol borane, has been developed. This system allows for the conversion of aryl and heteroaryl iodides, bromides, and several chlorides, containing a variety of functional groups, to the corresponding pinacol boronate esters. In addition to the increase in substrate scope, this is the first general method where relatively low quantities of catalyst and short reaction times can be employed.
- Billingsley, Kelvin L.,Buchwald, Stephen L.
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p. 5589 - 5591
(2008/12/20)
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- Synthesis and characterization of a light-emitting poly(p- phenylenevinylene)-based copolymer containing 1,3,4-oxadiazole functionality
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A new class of high brightness and luminance efficiency of poly[2-{4-[5-(3-(3,7-dimethyloctyloxy)phenyl)-1,3,4-oxadiazole-2-yl]phenyl}-1, 4-phenylenevinylene] (C10PhOxa-PPV) was synthesized by Gilch polymerization. The weight average molecular weight (Mw) and the polydispersity of C10PhOxa-PPV were found to be 2.7104 and 2.6, respectively. Double-layer light-emitting device with an ITO/PEDOT/C10PhOxa-PPV/Al was fabricated and characterized. The maximum brightness, and luminance efficiency of C10PhOxa-PPV showed values of up to 8.3cd/A and 4,426cd/m2, respectively.
- Jin, Sung-Ho,Kim, Sung-Chul,Shim, Jong-Min,Park, Sung-Min,Lee, Eun-Jae,Shin, Won Suk,Lee, Jae-Wook,Gal, Yeong-Soon
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p. 103 - 109
(2007/10/03)
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- Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies
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(Chemical Equation Presented) From chloride to boronate: Catalysts comprising palladium and biaryl monophosphine ligands provide highly active systems for the borylation of aryl and heteroaryl chlorides (see scheme). Symmetrical and unsymmetrical biaryl products can also be prepared directly from two aryl chlorides without isolation of the intermediate boronate esters. Computational studies provide insight into the roles of the biaryl phosphine ligand and the KOAc base in the catalytic cycle.
- Billingsley, Kelvin L.,Barder, Timothy E.,Buchwald, Stephen L.
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p. 5359 - 5363
(2008/03/18)
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- Synthesis and EL properties of light-emitting polymers by Gilch polymerization
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A new class of soluble PPV derivatives containing dimethyldodecylsilylphenyl unit as a pendant was synthesized by Gilch polymerization method. The resulting electroluminescent polymers showed good solubility, good film-forming ability onto the ITO substra
- Jin, Sung-Ho,Jeong, Hwan-Hee,Hwang, Chan-Koo,Moon, Seong-Bae,Lee, Jae Wook,Hwang, Jin-Taek,Gal, Yeong-Soon,Lee, Jin-Kook
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- Synthesis and characterization of an efficiently fluorescent poly(phenylenevinylene) possessing pendant dendritic phenyl groups
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We have synthesized a thermally stable and high molecular weight fluorescent poly-(phenylenevinylene) (PPV) incorporating side-chain-tethered dendritic phenyl groups (DENPPV) through Gilch route; this DENPPV has a low abundance of tolane-bisbenzyl defects
- Dinakaran,Hsiao, Shu-Min,Chou, Chia-Hung,Shu, So-Lin,Wei, Kung-Hwa
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p. 10429 - 10435
(2008/02/01)
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- The conversion of phenols to the corresponding aryl halides under mild conditions
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Mild, novel procedures have been developed for the syntheses of aryl halides from the corresponding phenols in modest to good yields via boronate ester intermediates.
- Thompson, Alicia L. S.,Kabalka, George W.,Akula, Murthy R.,Huffman, John W.
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p. 547 - 550
(2007/10/03)
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- Synthesis and luminescence properties of poly[2-(9,9-dihexylfluorene-2-yl)-1,4-phenylenevinylene] and its copolymers containing 2-(2-ethylhexyloxy)-5-methoxy-1,4-phenylenevinylene units
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A PPV derivative bearing the dihexylfluorenyl pendants, poly[2-(9,9-dihexylfluorene-2-yl)1,4-phenylenevinylene] (DHF-PPV) and its copolymers containing the dialkoxy-substituted phenylenevinylene units, i.e., poly[(2-(9,9-dihexylfluorene-2-yl)-1,4-phenylen
- Sohn, Byung-Hee,Kim, Kyungkon,Choi, Don Soo,Kim, Young Kwan,Jeoung, Sae Chae,Jin, Jung-Il
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p. 2876 - 2881
(2007/10/03)
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- Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate
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The borylation of arenes leads to the formation of synthetically versatile products from unactivated arene reagents. We report that Ir(I) precursors in conjunction with bipyridine ligands catalyze in high yields the borylation of arenes under mild conditions. These reactions encompase arenes bearing both electron-withdrawing and electron-donating substituents. The temperatures required for the transformation are much lower than those previously reported for direct arene borylation. The combination of [Ir(COE)2Cl]2 and (4,4-di-t-butyl)bipyridine even allows for reaction at room temperature. The same catalyst system at 100 °C provides remarkably high turnover numbers for a hydrocarbon functionalization process. Mechanistic studies show that the reactions involve uncommon, Ir(II) tris-boryl complexes. An example of this type of complex ligated by di-t-butylbipyridine was isolated and structurally characterized. It reacted rapidly at room temperature to produce aryl boronate esters in high yields. Copyright
- Ishiyama, Tatsuo,Takagi, Jun,Ishida, Kousaku,Miyaura, Norio,Anastasi, Natia R.,Hartwig, John F.
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p. 390 - 391
(2007/10/03)
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