19571-30-3Relevant academic research and scientific papers
Synthesis, characterization and antimalarial activity of isoquinoline derivatives
Theeramunkong, Sewan,Thiengsusuk, Artitiya,Vajragupta, Opa,Muhamad, Phunuch
, p. 109 - 119 (2020/10/12)
This paper presents synthesis of novel decorated isoquinolines that can be used as antimalarial agents. Two series of compounds, isoquinoline phenyl and isoquinoline triazole derivatives, were synthesized via the Suzuki–Miyaura and Sharpless–Fokin reactio
From the grafting of NHC-based Pd(II) complexes onto TiO2 to the in situ generation of Mott-Schottky heterojunctions: The boosting effect in the Suzuki-Miyaura reaction. Do the evolved Pd NPs act as reservoirs?
De Tovar, Jonathan,Rataboul, Franck,Djakovitch, Laurent
, p. 133 - 147 (2021/05/10)
The assumption that the real active species involved in the Suzuki-Miyaura reaction are homogeneous, heterogeneous or both is often proposed. However a lack of characterization of the true catalytic entities and their monitoring makes assumptions somewhat elusive. Here, with the aim of getting new insights into the formation of active species in the Suzuki-Miyaura reaction, a family of palladium(II) complexes bearing bis(NHC) ligands was synthesized for immobilization at the surface of TiO2. The studies reveal that once the complexes are anchored onto TiO2, the mechanism governing the catalytic reaction is different from that observed for the non-anchored complexes. All complexes evolved to Pd NPs at the surface of TiO2 under reaction conditions and released Pd species in the liquid phase. Also, this reactivity was boosted by the in situ generation of Mott-Schottky heterojunctions, opening new routes towards the design of heterogenized catalysts for their further implementation in reverse-flow reactors.
Carbonylative Acetylation of Heterocycles
Zhang, Youcan,Yin, Zhiping,Wu, Xiao-Feng
supporting information, p. 213 - 216 (2020/01/22)
Herein, a new procedure for the carbonylative acetylation of heterocycles has been developed. In this process, organic peroxide acts as the methyl source. Various heterocycles were transformed into the corresponding methyl heterocyclic ketones in moderate to good yields.
Synthesis of heterobiaryls via Suzuki-Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems
Liu, Leifang,Zhao, Kai,Li, Wenbo,Liu, Mingli,Chen, Yuting,Dong, Yan
, (2019/02/25)
A variety of heterobiaryl compounds have been synthesized by the Suzuki-Miyaura coupling reactions of heteroaryl halides with potassium aryltrifluoroborates. Pd (OAc)2 was found to be highly efficient for the Suzuki-Miyaura coupling reactions of various heteroaryl halides with potassium aryltrifluoroborates in aqueous systems, delivering the corresponding heterobiaryl compounds in good to excellent yields.
Benzimidazolyl Palladium Complexes as Highly Active and General Bifunctional Catalysts in Sustainable Cross-Coupling Reactions
Zhu, Jiancheng,Lindsay, Vincent N. G.
, p. 6993 - 6998 (2019/08/26)
A family of air- A nd moisture-stable dinuclear palladium complexes bearing 2-benzimidazolyl ligands is reported and shown to be a highly effective and general catalytic platform in diverse cross-coupling reactions. The rigidity and conformation of the ligand scaffold was readily modified via tethering of the 2-benzimidazolyl moiety to diamine ligands, resulting in significant changes in catalytic activity. Under optimal conditions, Suzuki, Heck, and Sonogashira-type couplings of aryl bromides can all be performed efficiently with good functional group compatibility using only 0.1 mola?% of catalyst, in aqueous or alcohol solvents. Experimental evidence highlights the importance of the bifunctional character of the ligand for catalytic activity, where the basic N-functionality in the ligand framework is proposed to accelerate (trans)metalation steps via intramolecular assistance.
Direct Arylation of Unactivated Alkanes with Heteroarenes by Visible-Light Catalysis
Huang, Cheng,Wang, Jing-Hao,Qiao, Jia,Fan, Xiu-Wei,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 12904 - 12912 (2019/09/09)
The functionalization of aliphatic C-H bonds is both a major challenge and a desirable goal in organic synthesis. Here, we describe the successful arylation of unactivated alkanes with heteroarenes by using iridium polypyridyl complexes as the photocatalyst and persulfate as the HAT catalyst precursor under visible-light irradiation. This reaction features good functional group tolerance and broad scope with regard to both alkane and heteroarene substrates (37 examples), which allows direct access to alkyl-substituted N-heteroarenes, a key structural motif in natural products and bioactive molecules.
Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature
Kazi, Imran,Guha, Somraj,Sekar, Govindasamy
, p. 6642 - 6654 (2019/06/14)
A halogen bond-assisted electron-catalyzed iodination of heteroarenes has been developed for the first time under atom economic condition at room temperature. The iodination is successful with just 0.55 equiv of iodine and 0.50 equiv of peroxide. The kinetic study indicates that the reaction is elusive in the absence of a halogen bond between the substrate and iodine. The formation of a halogen bond, its importance in lowering the activation barrier for this reaction, the presence of radical intermediates in a reaction mixture, and the regioselectivity of the reaction have been demonstrated with several control experiments, spectroscopic analysis, and quantum chemical calculations. Allowing the formation of the halogen bond may offer a new strategy to generate the reactive radical intermediates and to enable the otherwise elusive electron-catalyzed reactions under mild reaction conditions.
Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides
Dilauro, Giuseppe,Quivelli, Andrea Francesca,Vitale, Paola,Capriati, Vito,Perna, Filippo Maria
supporting information, p. 1799 - 1802 (2019/01/25)
Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.
Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines
Saini, Gaurav,Kumar, Pravin,Kumar, Gangam Srikanth,Mangadan, Arun Raj Kizhakkayil,Kapur, Manmohan
supporting information, p. 441 - 444 (2018/01/28)
A diverse array of isoquinolines and phenanthridines have been accessed by developing a two-step, one-pot method constituting regioselective palladium-catalyzed Kuwajima-Urabe α-arylation of silylenol ethers and acid-mediated deprotection, annulation, and aromatization. Structural diversity in the silylenol ethers leads to three different classes of isoquinolines and phenanthridines from which related natural products can be derived. The synthetic utility of this method by the quick assembly of the natural product trispheridine is also demonstrated.
Method for preparing bi-arene from aryl diazo salts and aryl sulfonylhydrazide
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Paragraph 0044; 0045; 0046, (2018/10/19)
The invention discloses a method for preparing bi-arene from aryl diazo salts and aryl sulfonylhydrazide. The method comprises the following steps of performing denitrification coupling reaction on aryl diazo salts and aryl sulfonylhydrazide in an organic solvent under the effects of palladium catalysts, ligands and additives; after the reaction is completed, performing post-treatment to obtain the bi-arene. The method provided by the invention has the advantages that the substrate price is low; the property is stable; the operation is convenient; meanwhile, the reaction yield is high; the substrate general applicability is high.
