82437-75-0Relevant academic research and scientific papers
Pd Nanoparticles Embedded Into MOF-808: Synthesis, Structural Characteristics, and Catalyst Properties for the Suzuki–Miyaura Coupling Reaction
Li, Tang,Pang, Wan,Wang, Jie,Zhang, Xiaoli,Zhao, Zesheng
, (2021/07/31)
Abstract: A heterogeneous single-site catalyst Pd@MOF-808 was successfully synthesized by water-based, green synthesis procedure. The catalytic experiments exhibited the Pd@MOF-808 promoted efficiently the Suzuki–Miyaura coupling reaction without the assistance of organic phosphine ligands at atmospheric pressure conditions. The catalyst also could be applied in the gram-scale synthesis of industrially anti-inflanmatory analgestic Fenbufen. Graphic Abstract: [Figure not available: see fulltext.]
Palladium Supported on Silk Fibroin for Suzuki–Miyaura Cross-Coupling Reactions
Albano, Gianluigi,Farinola, Gianluca M.,Lo Presti, Marco,Milella, Antonella,Omenetto, Fiorenzo G.,Rizzo, Giorgio
supporting information, p. 6992 - 6996 (2020/11/30)
Silk fibroin supported Pd (Pd/SF) has been prepared and used as catalyst in Suzuki–Miyaura cross-coupling reactions in water/ethanol (4:1 v/v) mixture. The reactions proceed rapidly with aryl iodides and boronic acids with different electronic properties using low metal loading (0.38 mol-%). Pd/SF exhibits better recyclability compared to other biopolymer-supported Pd catalysts, up to nineteen cycles without loss of activity.
Suzuki-Miyaura coupling catalyzed by a Ni(II) PNP pincer complex: Scope and mechanistic insights
Madera, Justin,Slattery, Megan,Arman, Hadi D.,Tonzetich, Zachary J.
, (2020/02/04)
The nickel(II) pincer complex, [NiCl(PhPNP)] (PhPNP = anion of 2,5-bis(diphenylphosphinomethyl)pyrrole), has been employed as a precatalyst for the Suzuki-Miyaura cross-coupling reaction of aryl halides and boronic acids. Both electron-rich and electron-deficient aromatic bromides were found to undergo coupling with boronic acids in modest yield at elevated temperature in the presence of K3PO4·H2O. Preliminary mechanistic studies of the reaction identified a novel species formulated as the boronate complex, [Ni(OB{OH}{2-tolyl})(PhPNP)], which most likely represents a catalyst deactivation pathway. The productive catalytic cycle was found to be most consistent with a Ni(I)/Ni(III) process where the boronic acid serves as both reductant and nucleophile in the presence of base.
Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
supporting information, (2019/05/07)
A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
The Rational Design and Synthesis of Water-Soluble Thiourea Ligands for Recoverable Pd-Catalyzed Aerobic Aqueous Suzuki-Miyaura Reactions at Room Temperature
Chen, Wei,Lu, Xiao-Yan,Xu, Bei-Hua,Yu, Wei-Guo,Zhou, Zi-Niu,Hu, Ying
, p. 1499 - 1510 (2018/01/17)
Eight precatalysts containing carboxylic-functionalized thiourea ligands are prepared and their activities and recyclability are evaluated in aerobic aqueous Suzuki-Miyaura reactions. A bulky monothiourea-Pd complex, functionalized with four carboxylic groups, shows the best activity and recyclability in the coupling of aryl bromides with arylboronic acids. The catalyst can be reused at least five times without any significant reduction in its catalytic activity. TEM analysis and the confirmed catalytic activity of the observed black precipitate reveal that Pd nanoparticles are formed during the reactions and are stabilized by the carboxylic-functionalized thiourea ligands.
A simple, quick and novel protocol for biaryl synthesis using LiCl-promoted in situ-generated Pd nanoparticles
Phukan, Parmita,Boruah, Preeti Rekha,Gehlot, Praveen Singh,Kumar, Arvind,Sarma, Diganta
, (2017/09/12)
This paper describes a simple and a very quick protocol for biaryl synthesis using the Suzuki–Miyaura cross-coupling reaction. A quintessential role of salting-out agent LiCl was observed in the Suzuki–Miyaura cross-coupling reaction that enhanced the red
A Highly Active Cobalt Catalyst System for Kumada Biaryl Cross-Coupling
Wu, Wenqin,Duong, Hung A.
supporting information, p. 1199 - 1202 (2018/03/23)
A highly active cobalt catalyst system has been developed for the cross-coupling reactions of arylmagnesium reagents and aryl bromides. In the presence of 1 mol% CoCl 2, 2 mol% IPr·HCl and 2 mol% NaO t Bu, a wide range of (hetero)biaryls are prepared in 51-99% yields at room temperature within a short reaction time.
A thiosemicarbazone–palladium(II)–imidazole complex as an efficient pre-catalyst for Suzuki–Miyaura cross-coupling reactions at room temperature in aqueous media
Baruah, Jayantajit,Gogoi, Rajjyoti,Gogoi, Nibedita,Borah, Geetika
, p. 683 - 692 (2017/09/06)
Abstract: A Pd(II) complex of two sterically crowded ligands, specifically an N,S-donor thiosemicarbazone and an N-donor imidazole, has been synthesized and characterized by physicochemical and spectroscopic methods. X-ray single-crystal analysis revealed that the coordination geometry around the palladium center is distorted square planar, and the chloride ligand is involved in intermolecular bifurcated X–HY-type (where X?=?C, N and Y?=?Cl) hydrogen bonding. This complex proved to be a highly active and retrievable pre-catalyst for additive-free Suzuki–Miyaura cross-coupling reactions of arylboronic acids with aryl bromides or chlorides at room temperature and 60?°C, respectively. The reactions require a low catalyst loading and the complex is converted to ~1.5–2.0 nm-sized Pd nanoparticles (probably the real catalyst). The catalyst can be reused up to seven times without significant loss in activity. Since the reaction proceeds under mild conditions in aqueous medium and the catalyst is recoverable, it provides an environmentally benign alternative to the existing protocols for Suzuki–Miyaura reactions. Graphical abstract: Biaryls can be synthesized in high yield under greener reaction conditions in the presence of efficient pre-catalyst, thiosemicarbazone–palladium(II)–imidazole.[Figure not available: see fulltext.].
tert-butoxide-promoted coupling of aryl iodides with arenes using Di-tert-butyl hyponitrite as an initiator
Kiriyama, Kazuya,Shirakawa, Eiji
supporting information, p. 1757 - 1759 (2017/11/23)
The coupling reaction of aryl iodides with arenes was found to proceed under mild conditions to give biaryls through a homolytic aromatic substitution mechanism, using potassium tert-butoxide and di-tert-butyl hyponitrite as a stoichiometric promoter and a radical initiator, respectively.
Palladium-catalyzed cross-coupling of aryl chlorides with arylsilatranes
Yamamoto, Yutaro,Baralle, Alexandre,Godefroy, Ana?s,Murakami, Kei,Yorimitsu, Hideki,Osuka, Atsuhiro
, p. 568 - 574 (2019/05/21)
The cross-coupling reactions of arylsilatranes with readily available and inexpensive aryl chlorides were carried out in toluene/THF at 100 °C for 3 h in the presence of tetrabutylammonium fluoride as an activator for smooth transmetalation and catalytic amounts of palladium(II) acetate and XPhos.
