- Palladium-Catalyzed Synthesis of Triphenylenes via Sequential C-H Activation and Decarboxylation
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A novel tandem intermolecular decarboxylative coupling reaction of o-bromobenzoic acids and aryl iodides has been developed. The method affords a range of unsymmetrically triphenylenes and displays unique regioselectivity and broad substrate scope. Mechanistically, palladium/norbornene-catalyzed C-H activation and subsequent double decarboxylative coupling reactions were involved. Moreover, the triphenylenes can also be synthesized from 2-iodobiphenyls and o-bromobenzoic acids under norbornene-free conditions.
- Yang, Yuzhong,Zhou, Bang,Zhu, Xiaoming,Deng, Guobo,Liang, Yun,Yang, Yuan
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- A novel compound, a method for preparing the same, and a negative active material for a redox flow battery including the new compound, and a redox flow battery comprising the same
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The present invention provides a novel compound having an excellent redox stability and a low reduction potential. The present invention relates to a negative active material for a redox flow battery comprising a novel compound and a novel compound, and a
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Paragraph 0111; 0114-0119; 0124-0126
(2021/08/24)
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- Modular metal-free catalytic radical annulation of cyclic diaryliodoniums to access π-extended arenes
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Polycyclic aromatic hydrocarbons (PAHs) are of increasing importance in the advanced material field. Cyclic diaryliodonium salts are non-toxic and environmentally benign arylating reagents. Here, we describe an alkylamine-mediated free radical intramolecular annulation to access PAHs under environmentally friendly conditions. On modulating substituents and their positions in the iodoniums, the free radical reaction controllably underwent three types of cyclization including ring contraction and ring switch to form tricyclic and tetracyclic frameworks of PAHs. Preliminary mechanistic studies implied that alkylamines initiated a radical pathway to complete the cyclization efficiently. Moreover, these acquired products were further converted into diverse complex graphene segments.
- Zhu, Daqian,Peng, Hui,Sun, Yameng,Wu, Zhouming,Wang, Yun,Luo, Bingling,Yu, Tiantian,Hu, Yumin,Huang, Peng,Wen, Shijun
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supporting information
p. 1972 - 1977
(2021/03/26)
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- Synthesis of Redox-Active Phenanthrene-Fused Heteroarenes by Palladium-Catalyzed C-H Annulation
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Pd-catalyzed C-H annulation reactions of halo- and aryl-heteroarenes were developed using readily available o-bromobiaryls and o-dibromoaryls, respectively. A variety of five-membered heteroarenes rapidly provided the corresponding phenanthrene-fused heteroarenes, which led to the identification of phenanthro-pyrazole and thiazole as new, stable -2 V redox couples. The flexible syntheses and tunability of the redox potentials of these azole-fused phenanthrenes over a wide range are expected to facilitate their application as redox-active organic functional materials.
- Jang, Jin Hyeok,Ahn, Seongmo,Park, Soo Eun,Kim, Soeun,Byon, Hye Ryung,Joo, Jung Min
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supporting information
p. 1280 - 1285
(2020/02/28)
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- Two-in-One Strategy for the Pd(II)-Catalyzed Tandem C-H Arylation/Decarboxylative Annulation Involved with Cyclic Diaryliodonium Salts
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We report here a two-in-one strategy for the Pd(II)-catalyzed tandem C-H arylation/decarboxylative annulation between readily available cyclic diaryliodonium salts and benzoic acids. The carboxylic acid functionality can be used as both a directing group for the ortho-C-H arylation and the reactive group for the tandem decarboxylative annulation. By a step-economical double cross-coupling annulation procedure, the privileged triphenylene frameworks were efficiently constructed, which have potential applications in material chemistry.
- Hu, Tao,Xu, Kai,Ye, Zenghui,Zhu, Kai,Wu, Yanqi,Zhang, Fengzhi
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supporting information
p. 7233 - 7237
(2019/10/02)
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- Synthesis of triphenylene derivatives by Pd-catalyzed Suzuki coupling/intramolecular C–H activation between arylboronic acids and dibromobiphenyls
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An efficient and regioselective synthesis of functionalized triphenylenes via palladium-catalyzed Suzuki-Miyaura coupling and subsequent intramolecular C–H activation between arylboronic acids and dibromobiphenyls was developed. This methodology showed excellent atomic economy and regiospecificity as well as synthetic feasibility of unsymmetrical triphenylenes.
- Tu, Jingxuan,Li, Gaoqiang,Zhao, Xiaoqian,Xu, Feng
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- An aryl substituted tris of compounds of preparation method and its application
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The invention discloses an aryl substituted tris of compounds of preparation method and its application. The preparation method process is: in formula I compound as a raw material, under protection of inert gas, in the organic solution, the participation of the inorganic base, to control the reaction temperature 70 - 160 °C, raw material process for the catalytic reaction to obtain aryl substituted tris benzene compound; type I structure of the compound is: Wherein R1 For the H atom, alkyl, alkoxy, haloalkyl oxy, F or Cl, R2 For the H atom, alkyl, alkoxy, haloalkyl oxy, F or Cl, and R1 And R2 In at least one is a H atom. This synthetic route has not seen the literature reports, and the cost of raw material; unit of simple operation, low equipment requirements, is suitable for the rapid construction of tris of compounds and fused ring compound.
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Paragraph 0018; 0022-0024
(2019/07/08)
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- Bottom-up Construction of π-Extended Arenes by a Palladium-Catalyzed Annulative Dimerization of o-Iodobiaryl Compounds
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A straightforward method was developed for construction of aromatic compounds with a triphenylene core. The method involves Pd-catalyzed annulative dimerization of o-iodobiaryl compounds by double C?I and C?H bond cleavage steps. Simple reaction conditions are needed, requiring neither a ligand nor an oxidant, and the reaction tolerates a wide range of coupling partners without compromising efficiency or scalability. Significantly, the tetrachloro-substituted synthon, 1,6,11-trichloro-4-(4-chlorophenyl)triphenylene, can be generated and used to prepare a series of fully fused, small graphene nanoribbons by a late-stage arylation with arylboronic acids and a subsequent Scholl reaction. The synthetic strategy enables bottom-up access to extended π-systems in a controlled manner.
- Zhu, Chendan,Wang, Di,Wang, Dingyi,Zhao, Yue,Sun, Wei-Yin,Shi, Zhuangzhi
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p. 8848 - 8853
(2018/05/08)
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- The mechanism of the photooxidation of 1-(9-phenanthryl)-4-phenyl-1-buten-3-yne
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Irradiation of 1-(9-phenanthryl)-4-phenylbutenyne (1) in aprotic solvents containing oxygen gives two products, namely a photocyclization product, 1-phenyltriphenylene 3, as is usually formed from diarylbutenynes, and photooxidation product (2), derived f
- Arendonk, R. J. F. M. van,Laarhoven, W. H.
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p. 263 - 267
(2007/10/02)
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- Syntheses and Physical Properties of Several Octiphenyls and a Septiphenyl
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Six symmetrical linear octiphenyls were synthesized by the Ullmann homo-coupling reaction of iodoquaterphenyl.Another satisfactory method for synthesizing octiphenyls is also described, i.e., a Kharash-type Grignard cross-coupling of biphenylylmagnesium bromide and diiodoquaterphenyl in the presence of bis(acetylacetonato)nickel(II).Moreover, m-septiphenyl was succesfully synthesized by deamination of the corresponding amino compound.Infrared studies of the polyphenyls indicated that the fine-structure bands in the regions of 770-810 and 870-915 cm-1 may be considered as indicators of the presence of consecutive m-phenylene rings, regardless of the existence of o- or p-phenylene rings.The ultraviolet spectra of the octiphenyls, which contain two kinds of linkages, showed absorption curves closely related to those of quaterphenyls corresponding to the structural units of the former compounds.The nuclear magnetic resonance spectra of the polyphenyls without an o-phenylene ring showed multiplet peaks due to the resonances of an isolated m-phenylene proton at the lowest field within a narrow region (δ 7.81-7.95).Hueckel molecular orbital calculations of the longest wavelength absorption bands of ten polyphenyls were carried out.The calculated and observed wavelengths were in rather good agreement except for the cases of three compounds.Keywords - Ullmann reaction; Ni-complex-catalyzed cross-coupling; octiphenyls; septiphenyls; IR; UV; NMR; MO; quaterphenyl derivatives; polyphenyls
- Ozasa, Shigeru,Fujioka, Yasuhiro,Fujiwara, Michiko,Ibuki, Eiichi
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p. 3210 - 3222
(2007/10/02)
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