- A highly efficient method for the copper-catalyzed selective synthesis of diaryl chalcogenides from easily available chalcogen sources
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An efficient protocol for copper-catalyzed C-S or C-Se bond formation between aryl iodides and easily available chalcogen sources leading to diaryl chalcogenides is reported. A variety of symmetrical diaryl sulfides and diaryl selenides were synthesized in good to excellent yields. Unsymmetrical diaryl sulfides were also obtained in moderate yields from two different aryl iodides by a one-pot tandem process. This strategy was further successfully utilized for the synthesis of 2-phenylbenzo[b]thiophene and of [1]benzothieno[3,2-b] benzothiophene. A new Cu-catalyzed one-pot approach for the selective synthesis of symmetrical diaryl chalcogenides and unsymmetrical diarylsulfides with use of Na2S or Se as chalcogen sources has been developed. Copyright
- Li, Yaming,Nie, Caiping,Wang, Huifeng,Li, Xiaoying,Verpoort, Francis,Duan, Chunying
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- Taming the Lewis Superacidity of Non-Planar Boranes: C?H Bond Activation and Non-Classical Binding Modes at Boron
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The rational design of a geometrically constrained boron Lewis superacid featuring exceptional structure and reactivity is disclosed. It enabled the formation of non-classical electron deficient B?H?B type of bonding, which was supported by spectroscopic and structural parameters as well as computational studies. Taming the pyramidal Lewis acid electrophilicity through weak coordinating anion dissociation enabled a series of highly challenging chemical transformations, such as Csp2?H and Csp3?H activation under a frustrated Lewis pair regime and the cleavage of Csp3?Si bonds. The demonstration of such rich chemical behaviour and flexibility on a single molecular compound makes it a unique mediator of chemical transformations generally restricted to transition metals.
- Berionni, Guillaume,Champagne, Beno?t,Chardon, Aurélien,Fusaro, Luca,Mahaut, Damien,Osi, Arnaud,Tumanov, Nikolay,Wouters, Johan
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supporting information
(2022/01/20)
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- Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
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An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
- Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
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p. 2707 - 2712
(2020/03/11)
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- Boron-containing heterocyclic compound and application thereof in organic photoelectric device
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The invention provides a boron-containing heterocyclic compound and application thereof in an organic photoelectric device. The boron-containing heterocyclic compound is represented by a general formula (1) shown in the description. The invention further provides application of a material produced from the boron-containing heterocyclic compound in an organic electroluminescence element and application of the organic electroluminescence element in an organic electroluminescence display device. The boron-containing heterocyclic compound provided by the invention has a structure similar to a boron heteroanthracene derivative and has a proper donor-acceptor structure, a relatively small deltaEst energy value and a proper HOMO/LUMO value, the high brightness, low voltage, high efficiency and long service life of an organic EL element can be realized, and meanwhile, a material prepared from the compound has relatively high heat stability, is capable of remarkably improving the light-emittingstability of the luminescent device and can be widely applied to OLED luminescent devices and display devices to be used as a luminescent layer main body material or a thermally active delayed fluorescence luminescent material.
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Paragraph 0134-0136
(2018/12/01)
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- High-Performance Dibenzoheteraborin-Based Thermally Activated Delayed Fluorescence Emitters: Molecular Architectonics for Concurrently Achieving Narrowband Emission and Efficient Triplet–Singlet Spin Conversion
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Thermally activated delayed fluorescence (TADF) materials, which enable the full harvesting of singlet and triplet excited states for light emission, are expected as the third-generation emitters for organic light-emitting diodes (OLEDs), superseding the conventional fluorescence and phosphorescence materials. High photoluminescence quantum yield (ΦPL), narrow-band emission (or high color purity), and short delayed fluorescence lifetime are all strongly desired for practical applications. However, to date, no rational design strategy of TADF emitters is established to fulfill these requirements. Here, an epoch-making design strategy is proposed for producing high-performance TADF emitters that concurrently exhibiting high ΦPL values close to 100%, narrow emission bandwidths, and short emission lifetimes of ≈1 μs, with a fast reverse intersystem crossing rate of over 106 s?1. A new family of TADF emitters based on dibenzoheteraborins is introduced, which enable both doped and non-doped TADF-OLEDs to achieve markedly high external electroluminescence quantum efficiencies, exceeding 20%, and negligible efficiency roll-offs at a practical high luminance. Systematic photophysical and theoretical investigations and device evaluations for these dibenzoheteraborin-based TADF emitters are reported here.
- Park, In Seob,Matsuo, Kyohei,Aizawa, Naoya,Yasuda, Takuma
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- Silicon-Heteroaromatic [FeFe] Hydrogenase Model Complexes: Insight into Protonation, Electrochemical Properties, and Molecular Structures
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To learn from Nature how to create an efficient hydrogen-producing catalyst, much attention has been paid to the investigation of structural and functional biomimics of the active site of [FeFe]-hydrogenase. To understand their catalytic activities, the μ
- Goy, Roman,Bertini, Luca,G?rls, Helmar,De Gioia, Luca,Talarmin, Jean,Zampella, Giuseppe,Schollhammer, Philippe,Weigand, Wolfgang
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p. 5061 - 5073
(2015/03/30)
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- Cu-catalyzed synthesis of diaryl thioethers and S -cycles by reaction of aryl iodides with carbon disulfide in the presence of DBU
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Diaryl thioethers and S-cycles were obtained on the basis of the copper-catalyzed reaction of carbon disulfide and aryl iodides in the presence of DBU. This reaction enables the one-pot synthesis of diaryl thioethers by employing cheap, available, and easy-to-handle carbon disulfide with aryl iodides. The reaction was successfully employed in the construction of sulfur-containing cyclic molecules.
- Zhao, Peng,Yin, Hang,Gao, Hongxin,Xi, Chanjuan
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p. 5001 - 5006
(2013/06/27)
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- Ligand-free copper-catalyzed synthesis of diaryl thioethers from aryl halides and thioacetamide
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Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 °C. Georg Thieme Verlag Stuttgart - New York.
- Tao, Chuanzhou,Lv, Aifeng,Zhao, Nan,Yang, Shuai,Liu, Xiaolang,Zhou, Jian,Liu, Weiwei,Zhao, Jing
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supporting information; experimental part
p. 134 - 138
(2011/03/22)
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