706-06-9Relevant academic research and scientific papers
Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes
Shi, Jun-Bin,Bu, Qingqing,Liu, Bin-Yuan,Dai, Bin,Liu, Ning
, p. 1850 - 1860 (2021/01/14)
An organocatalytic strategy for the direct carboxylation of terminal alkynes with CO2 has been developed. The combined use of a bifunctional organocatalyst and Cs2CO3 resulted in a robust catalytic system for the preparation of a range of propiolic acid derivatives in high yields with broad substrate scope using CO2 at atmospheric pressure under mild temperatures (60 °C). This work has demonstrated that this organocatalytic method offers a competitive alternative to metal catalysis for the carboxylation of terminal alkynes and CO2. In addition, this protocol was suitable for the three-component carboxylation of terminal alkynes, alkyl halides, and CO2.
N-Heterocyclic carbene-nitrogen molybdenum catalysts for utilization of CO2
Chen, Fei,Tao, Sheng,Liu, Ning,Dai, Bin
, (2021/01/19)
Three new N-heterocyclic carbene-nitrogen molybdenum complex was synthesized, and its catalytic activity was evaluated in the cycloaddition of epoxides with CO2. The molybdenum complex combined with tetrabutyl ammonium iodide (TBAI) resulted in a catalytic system for efficient conversion of a wide range of terminal and internal epoxides under 80 °C and 5–7 bar pressure for CO2. The cooperative catalysis mechanism between molybdenum complex and TBAI was elucidated, in which molybdenum complex was used as Lewis acid, and TBAI was employed as nucleophilic reagent. In addition, the NHC-Mo catalytic system was also successfully applied for the direct carboxylation of terminal alkynes with CO2.
Pre-carbonized nitrogen-rich polytriazines for the controlled growth of silver nanoparticles: Catalysts for enhanced CO2chemical conversion at atmospheric pressure
Liu, Jian,Zhang, Xiaoyi,Wen, Bingyan,Li, Yipei,Wu, Jingjing,Wang, Zhipeng,Wu, Ting,Zhao, Rusong,Yang, Shenghong
, p. 3119 - 3127 (2021/05/25)
High catalytic activity and sufficient durability are two unavoidable key indices of an efficient heterogeneous catalyst for the direct carboxylation of terminal alkynes with CO2 conversion. Nitrogen-rich covalent triazine frameworks (CTFs) are promising substrates, while random distribution of some residual -NH2 groups brings challenges to the controlled growth of catalytic species. Here, we adopt a pre-carbonization protocol, annealing below the carbonization temperature, to eliminate the random -NH2 groups in CTFs and meanwhile to promote polycondensation degree under the premise of maintaining the pore structure. Benefiting from the improved condensation and orderly N atoms, p-CTF-250, for which CTFs are annealed at 250 °C, exhibits improved CO2 adsorption capacity and the ability to control the growth of Ag NPs. Mono-dispersed Ag NPs are generated controllably and entrapped to form Ag@p-CTF-250 catalysts. These Ag@p-CTF-250 catalysts were employed in the direct carboxylation of various terminal alkynes with CO2 under mild conditions (50 °C, 1 atm) and showed excellent catalytic activity. In addition, these catalysts have robust recyclability and can be used for at least 5 catalytic runs while retaining yield above 90%. CO2 conversion proceeds well under the synergistic effect between the high CO2 capture capability and the uniform tiny Ag NPs in Ag@p-CTF-250 "nanoreactors". The results represent an efficient strategy for controlling the growth of metallic nanoparticles in porous organic polymer substrates containing disordered heteroatoms.
Microwave-assisted fabrication of a mixed-ligand [Cu4(μ3-OH)2]-cluster-based metal–organic framework with coordinatively unsaturated metal sites for carboxylation of terminal alkynes with carbon dioxide
Wang, Wen-Jing,Sun, Zhong-Hua,Chen, Sheng-Chun,Qian, Jun-Feng,He, Ming-Yang,Chen, Qun
, (2021/05/24)
The development of efficient and stable metal–organic framework (MOF) catalysts with coordinatively unsaturated metal sites for modern organic synthesis is greatly important. Herein, a robust [Cu4(μ3-OH)2]-cluster-based MOF (Cu-MOF) with a mixed-ligand system was successfully fabricated by a microwave-assisted method under mild conditions. The as-prepared Cu-MOF catalyst possessing unsaturated Cu (II) sites exhibited excellent catalytic activity toward the direct carboxylation of 1-ethynylbenzene with CO2, and various propiolic acid derivatives were synthesized in moderate to good yields under optimized reaction conditions. Furthermore, the catalyst remained stable and could be easily recycled for five sequential runs without incredible decrease in catalytic efficiency.
Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions
Xiao, Guorong,Wu, Kaifu,Zhou, Wei,Cai, Qian
supporting information, p. 4988 - 4991 (2021/10/14)
A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).
Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids
Ghosh, Subhankar,Ghosh, Rajat,Chattopadhyay, Shital K.
, (2020/09/15)
A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-
Design and Remarkable Efficiency of the Robust Sandwich Cluster Composite Nanocatalysts ZIF-8@Au25@ZIF-67
Yun, Yapei,Sheng, Hongting,Bao, Kang,Xu, Li,Zhang, Yu,Astruc, Didier,Zhu, Manzhou
supporting information, p. 4126 - 4130 (2020/03/05)
Heterogeneous catalysts with precise surface and interface structures are of great interest to decipher the structure-property relationships and maintain remarkable stability while achieving high activity. Here, we report the design and fabrication of the new sandwich composites ZIF-8@Au25@ZIF-67[tkn] and ZIF-8@Au25@ZIF-8[tkn] [tkn = thickness of shell] by coordination-assisted self-assembly with well-defined structures and interfaces. The composites ZIF-8@Au25@ZIF-67 efficiently catalyzed both 4-nitrophenol reduction and terminal alkyne carboxylation with CO2 under ambient conditions with remarkably improved activity and stability, compared to the simple components Au25/ZIF-8 and Au25@ZIF-8, highlighting the highly useful function of the ultrathin shell. In addition, the performances of these composite sandwich catalysts are conveniently regulated by the shell thickness. This concept and achievements should open a new avenue to the targeted design of well-defined nanocatalysts with enhanced activities and stabilities for challenging reactions.
Silver Nanoparticles Architectured HMP as a Recyclable Catalyst for Tetramic Acid and Propiolic Acid Synthesis through CO2 Capture at Atmospheric Pressure
Ghosh, Swarbhanu,Ghosh, Aniruddha,Riyajuddin, Sk,Sarkar, Somnath,Chowdhury, Arpita Hazra,Ghosh, Kaushik,Islam, Sk. Manirul
, p. 1055 - 1067 (2020/01/21)
The recent advancement on the tailored synthesis of hypercrosslinked microporous polymer (HMP-2) has assembled significant concentration by the virtue of its adjustable porosity, operative design and absolutely ordering structure. This perfectly structured Ag NPs supported carbocatalyst (Ag-HMP-2) has been synthesized by Friedel-Crafts alkylation between 4,4′-Bis(bromomethyl)-1,1′-biphenyl and carbazole over anhydrous iron(III)chloride catalysis followed by the appending of the silver nanoparticles (Ag NPs) onto the material. The silver nanoparticle was decorated over the HMP-2 to prepare the corresponding catalyst (Ag-HMP-2). The characterization of the newly produced material has been conducted by N2 adsorption/desorption studies, XPS, FE-SEM, transmission electron microscopy (TEM) and Powder X-ray diffraction (PXRD) methods. This microporous catalyst has spectacular activities for the production of tetramic acids from various types of propargylic amine derivatives at 60 °C under atmospheric carbon dioxide pressure. Parallel attempt on fixation of CO2 was executed over terminal alkynes to synthesize propiolic acids under 1 atm pressure. The catalyst (Ag-HMP-2) exhibited sufficient recycling ability for the generation of tetramic acids and propiolic acids up to five catalytic runs without reduction in its catalytic activity.
Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones
Yin, Congcong,Yang, Tao,Pan, Yingmin,Wen, Jialin,Zhang, Xumu
supporting information, p. 920 - 923 (2020/02/04)
A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.
Visible light induced 3-position-selective addition of arylpropiolic acids with ethersviaC(sp3)-H functionalization
Luo, Jun,Wan, Zi-Juan,Yuan, Xiao-Feng
supporting information, p. 3258 - 3262 (2020/05/14)
Although the 2-position-selective decarboxylative coupling or addition of arylpropiolic acids with cyclic ethers has been intensively investigated, selective functionalization of arylpropiolic acids at the 3-position is still a big challenge. Herein, an i
