329214-79-1Relevant articles and documents
Compounds comprising benzophenone group, Organic electronic device comprising organic layers comprising the photo-cured of the monomer compounds
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Paragraph 0293-0294; 0305-0306, (2021/03/09)
The compound represented by Formula I or II is provided as an organic material layer material of an organic electronic device. The benzophenone functional group-containing compound represented by the following Chemical I or Chemical Formula II: I (Chemical Formula Ar -) (R). 1 -R2 -Bpm In the formula, m is 1 and 10, and Ar is a substituted or unsubstituted m having a C-order linking group. 6 -C60 Substituted or unsubstituted m having aryl group, C nd-linking group3 -C60 Substituted or unsubstituted fused m with heteroaryl groups or C primary linking groups6 -C60 Aryl group, R1 And R2 Each independently represents a simple bond, O - a substituted or unsubstituted C. 6 -C30 Arylene group, substituted or unsubstituted C3 -C30 Heteroarylene group, substituted or unsubstituted C1 -C10 The alkylene group and Bp are 1 divalent linking groups derived from benzophenone functional groups. Chemical Formula II. In the formula, n is at least 1 and Ar ' is a substituted or unsubstituted m having a C-order linking group. 6 -C60 Aryl group Substituted or unsubstituted m having a C nd order linker3 -C60 Substituted or unsubstituted fused m with heteroaryl groups or C primary linking groups6 -C60 Aryl group, R3 And R4 Each independently represents a simple bond, O - a substituted or unsubstituted C. 6 -C30 Arylene group, substituted or unsubstituted C3 -C30 Heteroarylene group, substituted or unsubstituted C6 -C30 Fused arylene groups, substituted or unsubstituted C1 -C10 The alkylene group and Bp ' are 1 divalent linking groups derived from benzophenone functional groups.
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
supporting information, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
SYNTHESIS OF 5-(3-PYRIDYL)-2,2'-BITHIOPHENE(SENSITIZER)
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Page/Page column 11-12, (2021/02/05)
Disclosed herein is a novel simple, short process for synthesis of the photosensitizer, 5-(3-pyridyl)-2,2'-bithiophene.
Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates
Cai, Mingzhong,Huang, Bin,Luo, Chengkai,Xu, Caifeng
, (2021/12/02)
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.
Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
K?nig, Burkhard,Wang, Hua,Wang, Shun
supporting information, p. 1653 - 1665 (2021/06/17)
Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.
Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study
Barroso, Santiago,Joksch, Markus,Puylaert, Pim,Tin, Sergey,Bell, Stephen J.,Donnellan, Luke,Duguid, Stewart,Muir, Colin,Zhao, Peichao,Farina, Vittorio,Tran, Duc N.,De Vries, Johannes G.
supporting information, p. 103 - 109 (2020/12/22)
Aryl boronic acids and esters are important building blocks in API synthesis. The palladium-catalyzed Suzuki-Miyaura borylation is the most common method for their preparation. This paper describes an improvement of the current reaction conditions. By using lipophilic bases such as potassium 2-ethyl hexanoate, the borylation reaction could be achieved at 35 °C in less than 2 h with very low palladium loading (0.5 mol %). A preliminary mechanistic study shows a hitherto unrecognized inhibitory effect by the carboxylate anion on the catalytic cycle, whereas 2-ethyl hexanoate minimizes this inhibitory effect. This improved methodology enables borylation of a wide range of substrates under mild conditions.
Cross-Coupling through Ag(I)/Ag(III) Redox Manifold
Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie
supporting information, p. 15396 - 15405 (2021/10/12)
In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.
Enzyme-like Supramolecular Iridium Catalysis Enabling C?H Bond Borylation of Pyridines with meta-Selectivity
Al-Shehimy, Shaymaa,Gramage-Doria, Rafael,Roisnel, Thierry,Trouvé, Jonathan,Zardi, Paolo
supporting information, p. 18006 - 18013 (2021/05/07)
The use of secondary interactions between substrates and catalysts is a promising strategy to discover selective transition metal catalysts for atom-economy C?H bond functionalization. The most powerful catalysts are found via trial-and-error screening due to the low association constants between the substrate and the catalyst in which small stereo-electronic modifications within them can lead to very different reactivities. To circumvent these limitations and to increase the level of reactivity prediction in these important reactions, we report herein a supramolecular catalyst harnessing Zn???N interactions that binds to pyridine-like substrates as tight as it can be found in some enzymes. The distance and spatial geometry between the active site and the substrate binding site is ideal to target unprecedented meta-selective iridium-catalyzed C?H bond borylations with enzymatic Michaelis–Menten kinetics, besides unique substrate selectivity and dormant reactivity patterns.
Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes
Tian, Ya-Ming,Guo, Xiao-Ning,Krummenacher, Ivo,Wu, Zhu,Nitsch, J?rn,Braunschweig, Holger,Radius, Udo,Marder, Todd B.
supporting information, p. 18231 - 18242 (2020/11/02)
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.
Compounds comprising benzophenone group, Organic electronic device comprising organic layers comprising the photo-cured of the monomer compounds
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Paragraph 0298; 0310-0311, (2020/08/12)
The present invention provides a compound containing a benzophenone functional group represented by chemical formula I: Ar-(R_1-R_2-Bp)_m or chemical formula II as a material for an organic material layer of an organic electronic device, wherein the compound is the compound containing the benzophenone functional group.COPYRIGHT KIPO 2020
