56862-34-1Relevant academic research and scientific papers
Controllable encapsulation of silver nanoparticles by porous pyridine-based covalent organic frameworks for efficient CO2conversion using propargylic amines
Bai, Guoyi,Chen, Ligong,He, Xingyue,Lan, Xingwang,Ricardez-Sandoval, Luis,Wang, Juan,Yan, Fanyong,Zhang, Yize
supporting information, p. 930 - 940 (2022/02/02)
The conversion of CO2 into value-added chemicals is an attractive alternative to produce valuable fuels and chemicals. In this work, we demonstrate two pyridine-based covalent organic frameworks (COFs) with rich porosity for the size-controlled synthesis
Non-Noble-Metal Metal-Organic-Framework-Catalyzed Carboxylative Cyclization of Propargylic Amines with Atmospheric Carbon Dioxide under Ambient Conditions
Gu, Ai-Ling,Wang, Wan-Ting,Cheng, Xin-Yu,Hu, Tian-Ding,Wu, Zhi-Lei
supporting information, p. 13425 - 13433 (2021/08/30)
The coupling reaction of propargylic amines and carbon dioxide (CO2) to synthesize 2-oxazolidinones is an important reaction in industrial production, and yet harsh reaction conditions and noble-metal catalysts are often required to achieve high product yields. Herein, one novel noble-metal-free three-dimensional framework, [Mg3Cu2I2(IN)4(HCOO)2(DEF)4]n (1), assembled by magnesium and copper clusters was synthesized and applied to this reaction. Compound 1 displays excellent solvent stability. Importantly, 1, acting as heterogeneous catalyst, can highly catalyze the cyclization of propargylic amines with CO2 under atmospheric pressure at room temperature, which can be recycled at least five times without an obvious decrease of the catalytic activity. NMR spectroscopy, coupled with 13C-isotope- and deuterium-labeling experiments, clearly clarifies the mechanism of this catalytic system: CO2 was successfully captured and converted to the product of 2-oxazolidinones, the CC bond of propargylic amines can be effectively activated by 1, and proton transfer was involved in the reaction process. Density functional theory calculations are further conducted to uncover the reaction path and the crucial role of compound 1 during the reaction.
Highly Efficient Conversion of Propargylic Amines and CO2 Catalyzed by Noble-Metal-Free [Zn116] Nanocages
Cao, Chun-Shuai,Cheng, Peng,He, Liang-Nian,Shi, Ying,Song, Zhen-Jun,Xia, Shu-Mei,Xu, Hang,Zhao, Bin
supporting information, p. 8586 - 8593 (2020/03/26)
The reaction of propargylic amines and CO2 can provide high-value-added chemical products. However, most of catalysts in such reactions employ noble metals to obtain high yield, and it is important to seek eco-friendly noble-metal-free MOFs catalysts. Here, a giant and lantern-like [Zn116] nanocage in zinc-tetrazole 3D framework [Zn22(Trz)8(OH)12(H2O)9?8 H2O]n Trz=(C4N12O)4? (1) was obtained and structurally characterized. It consists of six [Zn14O21] clusters and eight [Zn4O4] clusters. To our knowledge, this is the highest-nuclearity nanocages constructed by Zn-clusters as building blocks to date. Importantly, catalytic investigations reveal that 1 can efficiently catalyze the cycloaddition of propargylic amines with CO2, exclusively affording various 2-oxazolidinones under mild conditions. It is the first eco-friendly noble-metal-free MOFs catalyst for the cyclization of propargylic amines with CO2. DFT calculations uncover that ZnII ions can efficiently activate both C≡C bonds of propargylic amines and CO2 by coordination interaction. NMR and FTIR spectroscopy further prove that Zn-clusters play an important role in activating C≡C bonds of propargylic amines. Furthermore, the electronic properties of related reactants, intermediates and products can help to understand the basic reaction mechanism and crucial role of catalyst 1.
Efficient and Recyclable Cobalt(II)/Ionic Liquid Catalytic System for CO2 Conversion to Prepare 2-Oxazolinones at Atmospheric Pressure
Zhou, Zhi-Hua,Chen, Kai-Hong,He, Liang-Nian
supporting information, p. 1223 - 1228 (2019/11/21)
Converting CO2 into value-added chemicals represents a promising way to alleviate the CO2 derived environmental issues, for which the development of catalysts with high efficiency and recyclability is very desirable. Herein, the catalytic system by combining cobalt source and ionic liquid (IL) has been developed as the efficacious and recyclable catalyst for the carboxylative cyclization of propargylic amine and CO2 to prepare 2-oxazolinones. In this protocol, various propargylic amines were successfully transformed into the corresponding 2-oxazolinones with CoBr2 and diethylimidazolium acetate ([EEIM][OAc]) as the catalyst under atmospheric CO2 pressure. It is worth noting that the turnover number (TON) of this transformation can be up to 1740, presumably being attributed to the cooperative effect of the cobalt and IL. Furthermore, the existence of IL enables the catalytic system to be easily recycled to 10 times without losing its activity.
Metal Acetylide Elimination: The Key Step in the Cascade Decomposition and Transformation of Metalated Propargylamines
Flynn, Matthew T.,Blair, Victoria L.,Andrews, Philip C.
supporting information, p. 1225 - 1228 (2018/04/30)
Metal acetylide elimination facilitates a novel one-pot cascade metalation and elimination/addition route to a series of unsymmetrical secondary amines from the reaction of secondary propargylamines with organometallic reagents. Spectroscopic evidence suggests a dimetalated amido intermediate rather than an allene.
Facile entry to 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazin-6-ones from amines and amino acids
Sai Sudhir,Nasir Baig,Chandrasekaran, Srinivasan
scheme or table, p. 2423 - 2429 (2009/04/06)
A practical and high-yielding regioselective synthesis of several enantiopure 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]-pyrazin-6-ones is described starting from primary amines and α-amino acid derivatives in a three-step reaction sequence by employing a constrained intramolecular "click" reaction as the key step. The method obviates chromatographic purification of products. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
A facile method for the stereoselective preparation of (1E,3E)-4-substituted-1-amino-1,3-dienes via 1,4-elimination
Tayama, Eiji,Sugai, Sayaka
, p. 6163 - 6166 (2008/03/12)
The 1,4-elimination reaction of 1-amino-4-methoxy-(2Z)-alkenes is shown to proceed with high (1E,3E)-stereoselectivities to afford the corresponding 4-substituted-1-amino-1,3-dienes in good yield. The scope and stereochemical features of the synthetic met
