17164-77-1Relevant academic research and scientific papers
Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
Takahashi, Rikuro,Seo, Tamae,Kubota, Koji,Ito, Hajime
, p. 14803 - 14810 (2021/12/09)
The Suzuki–Miyaura cross-coupling between polyfluorinated arylboron nucleophiles and aryl halides enables the efficient construction of polyfluorinated structural motifs frequently found in organic materials and catalysts. A key challenge associated with
Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines
Cai, Tao,Feng, Chengjie,Shen, Fangqi,Bian, Kejun,Wu, Chunlei,Shen, Runpu,Gao, Yuzhen
, p. 653 - 656 (2020/12/23)
An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.
C-H Arylation of Thiophenes with Aryl Bromides by a Parts-per-Million Loading of a Palladium NNC-Pincer Complex
Purta, Anggi Eka,Ichii, Shun,Tazawa, Aya,Uozumi, Yasuhiro
supporting information, p. 1634 - 1638 (2020/08/28)
A palladium NNC-pincer complex efficiently catalyzed the direct arylation of thiophene derivatives with extremely low palladium loadings of the order of parts per million. Thus, the reaction of various thiophenes with aryl bromides in the presence of 25-100 mol ppm of chlorido[(2-phenyl-κ- C 2)-9-phenyl-1,10-phenanthroline-κ 2- N, N ′]palladium(II) NNC-pincer complex, K 2CO 3, and pivalic acid in N, N -dimethyl acetamide afforded the corresponding 2- or 5-arylated thiophenes in good to excellent yields. A combination of the present C-H arylation and Hiyama coupling with the same NNC-pincer complex provides an efficient synthesis of unsymmetrical 2,5-thiophenes with catalyst loadings at mol ppm levels.
Method for preparing benzothiophene compounds by silver oxide catalysis method
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Paragraph 0057-0061, (2019/12/02)
The invention provides a method for preparing benzothiophene compounds through a silver oxide catalysis method, and belongs to the technical field of heterocyclic compound preparation. In the presenceof an acidic solvent, the 2-acetenyl diphenyl sulfide a
Iridium-catalyzed Decarbonylative Coupling of Acyl Fluorides with Arenes and Heteroarenes via C-H Activation
Sakurai, Shun,Yoshida, Tomoki,Tobisu, Mamoru
supporting information, p. 94 - 97 (2019/01/23)
The first method for decarbonylative direct arylation using acyl fluorides is reported. This reaction proceeds, only when acyl fluorides are used, and other acyl halides cannot be used. The reaction can be applied to the direct arylation of a variety of substrates, including xylene, quinoline, and benzothiophene.
A sustainable heterogenized palladium catalyst for Suzuki-Miyaura cross coupling reaction of azaheteroaryl halides in aqueous media
Ganesamoorthy,Muthu Tamizh,Shanmugasundaram,Karvembu
, p. 76 - 85 (2018/03/23)
A unique recyclable Pd catalyst (‘SiO2’-NH2-Pd) for Suzuki-Miyaura coupling reaction of azaheteroaryl halides is developed. The catalytic system is working under mild aqueous condition with low Pd loading and without the use of phosphine ligand. The plausible mechanism is proposed based on the formation of undesired symmetrical biaryl from the coupling reaction of azaheteroaryl chlorides due to the oxidative homocoupling of nucleophilic arylboronic acid. This catalytic system represents an attractive and promising approach for the synthesis of azaheterobiaryls with high product yields. The catalyst has demonstrated an excellent recyclability.
Palladium/Copper Dual Catalysis for the Cross-Coupling of Aryl(trialkyl)silanes with Aryl Bromides
Komiyama, Takeshi,Minami, Yasunori,Furuya, Yuki,Hiyama, Tamejiro
supporting information, p. 1987 - 1990 (2018/02/10)
Whereas aryl(trialkyl)silanes are considered to be ideal organometallic reagents for cross-coupling reactions owing to their stability, low toxicity, solubility, and easy accessibility, they are generally inert under typical cross-coupling conditions. Disclosed herein is a palladium/copper catalytic system that enables the cross-coupling of trimethyl, triethyl, tert-butyldimethyl, and triisopropyl aryl silanes with aryl bromides. This process is applicable to the sequential C?H and C?Si bond arylation of thiophenes and the synthesis of poly(thiophene–fluorene)s.
Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions
Jiang, Pengcheng,Che, Xingzong,Liao, Yunfeng,Huang, Huawen,Deng, Guo-Jun
, p. 41751 - 41754 (2016/05/24)
A base-mediated 2-aryl substituted benzothiophene formation from 2-bromobenzene aldehydes, benzylic esters and elemental sulfur under transition-metal-free conditions is described. Various 2-aryl substituted benzothiophene were efficiently obtained under mild conditions.
Palladacycles derived from arylphosphinamides for mild Suzuki-Miyaura cross-couplings
Wu, Guo-Jie,Han, Fu-She,Zhao, Yu-Long
, p. 69776 - 69781 (2015/09/01)
We present a type of palladacyclic complexes derived from arylphosphinamides which can be used as efficient and versatile precatalysts for mild Suzuki-Miyaura cross-coupling. With the presence of 1.0 mol% of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be very easily prepared through a two-step procedure from the readily affordable diphenyl-phosphinic chloride and exhibit excellent stability toward air and moisture. Due to these prominent properties, the new palladacycles would find practical use in Suzuki-Miyaura couplings.
Phosphine-free palladium-catalysed direct C2-arylation of benzothiophenes with aryl bromides
Zhao, Liqin,Bruneau, Christian,Doucet, Henri
, p. 7082 - 7089 (2013/07/26)
Ligand-free Pd(OAc)2 was found to catalyse very efficiently the direct C2-arylation of benzothiophene derivatives under low catalyst concentration. The reaction can be performed employing as little as 0.5-0.1 mol % catalyst with electron-deficient and some electron-rich aryl bromides. The presence of a methyl or a formyl substituent at C3 of benzothiophene has a minor influence on the reactivity, and even a bromo substituents at C3 is tolerated. A wide variety of functional groups on the aryl bromide, such as nitrile, nitro, acetyl, formyl, ester, chloro, fluoro or trifluoromethyl has been employed.
