82366-97-0Relevant academic research and scientific papers
A Convoluted Polyvinylpyridine-Palladium Catalyst for Suzuki-Miyaura Coupling and C?H Arylation
Ohno, Aya,Sato, Takuma,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
supporting information, p. 4687 - 4698 (2020/09/07)
The development of highly active and reusable supported catalysts for Suzuki-Miyaura coupling and catalytic C?H arylation is important for fundamental and applied chemistry, with these reactions being used to produce medical compounds and functional materials. Herein, we found that a mesoporous composite made of a linear poly(4-vinylpyridine) and tetrachloropalladate acted as a dual-mode catalyst for a variety of cross-coupling reactions, with both Pd nanoparticles and a Pd complex catalyst being observed under different conditions. The polyvinylpyridine-palladium composite 1 was readily prepared via the molecular convolution of poly(4-vinylpyridine) and sodium tetrachloropalladate to provide a hardly soluble polymer-metal composite. The Suzuki-Miyaura coupling and the C?H arylation of aryl chlorides and bromides with arylboronic acids, thiophenes, furans, benzene, and anisole proceeded in the presence of 0.004 mol% (40 mol ppm) to 1 mol% Pd of 1 to afford the corresponding coupling products in high yields. Furthermore, the catalyst was reused without an appreciable loss of activity. Pharmaceutical compounds and functional materials were synthesized via the coupling reactions. N2 gas adsorption/desorption analysis indicated that the catalyst had a mesoporous nature, which played a crucial role in the catalysis. In the Suzuki-Miyaura couplings, in situ generated palladium nanoparticles in the polymer matrix were catalytically active, while a polymeric Pd(II) complex was crucial in the C?H arylations. These catalytic species were investigated via XAFS, XPS, far-infrared absorption, and Raman spectroscopies, as well as DFT calculations. (Figure presented.).
Method for catalyzing terminal alkene and powdered sulfur with copper to react in water phase to generate thiophene ring
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Paragraph 0004; 0022, (2016/10/10)
The invention discloses a method for catalyzing terminal alkene and powdered sulfur to react in a pure water phase to prepare a thiophene derivative. A water-soluble complex is used as a catalyst, and a one-pot reaction is conducted in the pure water phas
Trisulfur radical anion as the key intermediate for the synthesis of thiophene via the interaction between elemental sulfur and NaO t Bu
Zhang, Guoting,Yi, Hong,Chen, Hong,Bian, Changliang,Liu, Chao,Lei, Aiwen
supporting information, p. 6156 - 6159 (2015/01/16)
A facile base-promoted sulfur-centered radical generation mode and a single-step protocol for the synthesis of thiophene derivatives using 1,3-diynes via the interaction between elemental sulfur and NaOtBu has been reported. EPR experiments revealed that the trisulfur radical anion acts as a key intermediate of this process. A plausible mechanism has been proposed.
Copper(I)-catalyzed synthesis of 2,5-disubstituted furans and thiophenes from haloalkynes or 1,3-diynes
Jiang, Huanfeng,Zeng, Wei,Li, Yibiao,Wu, Wanqing,Huang, Liangbing,Fu, Wei
scheme or table, p. 5179 - 5183 (2012/07/03)
A regioselective synthesis of 2,5-disubstituted furans using copper(I) catalyst from haloalkynes in a one-pot procedure has been reported. This chemistry proceeds through the hydration reaction of 1,3-diynes, which can be readily prepared from the coupling reaction of haloalkynes in the presence of CuI. The procedure also can be used for the facile synthesis of 2,5-disubstituted thiophenes.
Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira-Glaser cyclization sequence
Urselmann, Dominik,Antovic, Dragutin,Mueller, Thomas J. J.
, p. 1499 - 1503 (2011/12/22)
Based upon a consecutive one-pot Sonogashira-Glaser coupling-cyclization sequence a variety of 2,5-di(hetero)arylthiophenes were synthesized in moderate to good yields. A single Pd/Cu-catalyst system, without further catalyst addition, and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.
A NOVEL PHOTOREARRANGEMENT OF 2,5-DIARYL-1,4-DITHIIN-1,1-DIOXIDE ACCOMPANIED BY EXTRUSION OF SULFUR DIOXIDE
Kobayashi, Keiji,Mutai, Kiyoshi
, p. 1461 - 1462 (2007/10/02)
Photolysis of the title compound afforded 2,5-diarylthiophene.The mechanism involving the valence isomerization to the thioketone was supported by the photolysis in n-butylamine, which gave pyrrole derivatives.
