Catalysts
·
2025
·Vol. 15
·期 3
·279
·
IF 4
Duozhen Chai,Chongli Wang,Jinzhen Liu,Dongfeng Cao,Kaixuan Guo,Yuankun Wang,Ye Yuan,Francis Verpoort
The cyclization of propargyl alcohols with CO2represents a highly significant method for the utilization of CO2. The resulting cyclic carbonates possesses high chemical value and hold great potential for applications in battery electrolytes, polymer precursors, and pharmaceutical intermediates. However, most existing reports on this cyclization have been limited to simple propargyl alcohol substrates that are substituted with inert alkyl, cycloalkyl, and phenyl groups. For functionalized propargyl alcohols, such as alkyne-1,2-diols, only a single report has been documented thus far. In this study, we have developed an innovative catalytic system comprising cost-effective copper salts and environmentally friendly ionic liquids (CuCl/1-ethyl-3-methylimidazolium acetate) for the cyclization of alkyne-1,2-diols with CO2. Compared to the previously reported AgF/bulky monophosphine ligand (BrettPhos) system, our system is free of traditional volatile solvents, phosphine ligands, and additives. Notably, this is the first reported Cu(I)-catalyzed system for this cyclization, offering significant advantages in terms of cost-effectiveness and reduced toxicity compared to silver salts. Moreover, the use of ionic liquids ensures considerable recyclability, further enhancing the sustainability and practicality of this approach.
研究领域:
化学
·
环境科学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
CHINESE JOURNAL OF CATALYSIS
·
2019
·
IF 4.914
Zhi-Hua Zhou,Xiao Zhang,Yong-Fu Huang,Kai-Hong Chen,Liang-Nian He
Inexpensive and efficient Cu(I) catalysis is reported for the synthesis of α-hydroxy ketones from propargylic alcohols, CO 2 , and water via tandem carboxylative cyclization and nucleophilic addition reaction. Notably, hydration of propargylic alcohols can be carried out smoothly under atmospheric CO 2 pressure, generating a series of α-hydroxy ketones efficiently and selectively. This strategy shows great potential for the preparation of valuable α-hydroxy ketones by using CO 2 as a crucial cocatalyst under mild conditions.
研究领域:
有机化学
·
催化化学
✓ 已验证
DOI
高影响因子
JOURNAL OF ORGANIC CHEMISTRY
·
2020
·
IF 4.335
Lujia Mao,Chunlei Li,Libo Xiang,Dejun Fu,Wangyang Ma,Qing Ye
The synthesis of allenyl-Bdan has been realized via the Cu(I)-catalyzed borylation of propargylic alcohols. This methodology offers a facile and efficient pathway toward allenyboronates with diverse functional groups due to the simple access to the substrates. The substrates bearing ester groups are well-tolerated in the synthesis of allenyl-Bdan under the Lewis acidic conditions. The structures of two allenyl-Bdan were further confirmed via single-crystal X-ray diffraction.
研究领域:
有机化学
·
合成化学
✓ 已验证
DOI
PubMed
高影响因子
CHEMPHYSCHEM
·
2017
·Vol. 18
·期 22
·3182-3188
·
IF 3.075
Xue-Dong Li,Qing-Wen Song,Xian-Dong Lang,Yao Chang,Liang-Nian He
Graphical Heterocycle promotion : An Ag 2 O/TMG (1,1,3,3-tetramethylguanidine) promoted substrate-driven and divergent route leads to a variety of heterocycles from propargyl alcohols, CO 2 , and 2-aminoethanols with turnover numbers up to 1260. The reaction proceeds through a cascade pathway with α-alkylidene cyclic carbonate as the intermediate. Chemical valorization of CO 2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO 2 , and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag 2 O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO 2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO 2 .
研究领域:
有机化学
·
绿色化学
✓ 已验证
DOI
PubMed
高影响因子
RSC Advances
·
2016
·Vol. 6
·期 59
·54020-54026
·
IF 3.289
Jikuan Qiu,Yuling Zhao,Huiyong Wang,Guokai Cui,Jianji Wang
Development of new efficient catalytic systems for chemical transformation of CO2 is a very attractive topic in green chemistry. In this work, we studied the synthesis of α-alkylidene cyclic carbonates through the coupling reaction between propargylic alcohols and CO2 with new silver catalysts. It was found that activated carbon supported AgX (X = Br and I) was a simple and efficient catalyst for the carboxylative cyclization of propargyl alcohols with CO2 at atmospheric pressure and room temperature. Nearly 99% yield of the desired product was obtained, and the product could be simply separated through solvent extraction. Moreover, the catalyst could be easily recovered and reused at least ten times without a decrease in the catalytic activity and selectivity. These findings are useful for the development of an environmentally friendly chemical process for the production of α-alkylidene cyclic carbonates.
研究领域:
绿色化学
·
催化化学
✓ 已验证
产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2021
·
IF 8.198
Jiajia Liu,Xiaochen Tang,Huiling Lu,Yingjie Xu
To reveal the interactions between azole-anion-based ionic liquids (AILs) and propargyl alcohol (PA) and their effect on the carboxylative cyclization reaction of PA with CO2, three AILs, namely, [P66614][Im], [P66614][4-MeIm], and [P66614][4-BrIm], were synthesized and characterized. The interactions between the AILs with 2-methyl-3-butyn-2-ol (MBY) were investigated through IR and 1H NMR spectra and DFT calculations. The results indicate that azole-based anions can form H-bonds with the hydroxyl (O–H) and the alkynyl hydrogen atoms (C≡C–H) of MBY simultaneously, with the former much stronger than the latter, which is supported by the interaction energy and the distance of the H-bond from DFT calculations. Interestingly, the strength of the former always increases with the mole fraction of AIL (xAIL), while that of the latter first decreases and then increases, reaching a minimum at xAIL ≈ 0.4. Furthermore, the order of the strength of the two H-bonds is as follows: [P66614][Im] > [P66614][4-MeIm] > [P66614][4-BrIm], which is in good agreement with their basicity. According to the interactions between the AILs with MBY and combined with the reaction mechanism of MBY with CO2 promoted by AILs, it is evident that the increase in the basicity of the AILs enhances the H-bond between the AILs with O–H, thereby enhancing the activation of MBY and the subsequent CO2 conversion. However, this will also increase the interaction between AILs and C≡C–H, resulting in the deprotonation of C≡C–H and hindering the activation of MBY. Therefore, choosing a suitable basic AIL and controlling its ratio are the keys to the reaction of PA and CO2.
研究领域:
化学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
Data in Brief
·
2018
·
IF 0
Dandan Song,Di Li,Xuan Xiao,Cheng Chen,Somboon Chaemchuen,Ye Yuan,Francis Verpoort
Data presented here are related with the research article entitled “Synthesis of ß -oxopropylcarbamates in a recyclable AgBr/ionic liquid catalytic system: An efficient assembly of CO 2 under ambient pressure” (Song et al., 2018) [1] . In this data article, the general synthetic procedures of ß-oxopropylcarbamates through the three-component reaction of propargylic alcohols, secondary amines and carbon dioxide (CO 2 ) catalyzed by a recyclable AgBr/ionic liquid (IL) system under mild pressure are described. Furthermore, the process for recycling the catalysts is supplied as well. Specifically, the investigative data for the temperature, amount of ILs, reaction time as well as the state of silver in the system are also reported. Finally, all the target products are confirmed by 1 H NMR, 13 C NMR, and high-resolution mass spectroscopy (HR-MS).
研究领域:
有机化学
·
绿色化学
✓ 已验证
DOI
PubMed
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2024
·Vol. 26
·期 1
·62
·
IF 4.9
Yuankun Wang,Chongli Wang,Weidong Lin,Qin Wang,Baisong Li,Cheng Chen,Ye Yuan,Francis Verpoort
α-Hydroxy ketones are a crucial class of organic compounds prevalent in natural products and pharmaceutical molecules. The CO2-promoted hydration of propargylic alcohols is an efficient method for the synthesis of α-hydroxy ketones. Herein, an ionic liquid (IL) was designed to catalyze this reaction individually under atmospheric CO2pressure, volatile organic solvents, and additives. This IL, constructed from the molybdate anion, can be recycled from industrial (NH4)2MoO4production wastewater, demonstrating its high tolerance to catalytic environments and significant potential for practical applications. To our knowledge, this is the first instance of an oxometallate-based IL catalyst being utilized for the CO2-promoted hydration of propargylic alcohols. Further mechanistic studies revealed the bifunctionality of this IL in activating both CO2and substrates.
研究领域:
有机化学
·
催化化学
·
绿色化学
✓ 已验证
DOI
PubMed
高影响因子
TETRAHEDRON
·
2019
·
IF 2.379
Jingyuan Li,Qingwen Song,Hengxuan Zhang,Ping Liu,Kan Zhang,Junwen Wang,Dengsong Zhang
Chemical fixation of carbon dioxide under mild reaction conditions e.g. atmospheric pressure and low temperature depends upon the ability of catalyst. Herein, a synergistic catalytic scheme of silver sulfadiazine/ n Bu 4 NBr was described for the three-component reaction of propargylic alcohols, CO 2 , and monohydric alcohols. This catalytic system was demonstrated effectively to provide β-oxopropyl carbonates in excellent yields (up to 99% yield with 5 mol% catalyst). The method tolerated a wide scope of propargylic alcohols and monohydric alcohols under atmospheric CO 2 pressure and solvent-free conditions. The excellent catalytic performance was attributed to the synergistic catalysis confirmed by the careful experiments.
研究领域:
催化
·
有机化学
·
绿色化学
✓ 已验证
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2020
·
IF 7.632
Di Li,Yanyan Gong,Minchen Du,Chao Bu,Cheng Chen,Somboon Chaemcheun,Jia Hu,Yongxing Zhang,Ye Yuan,Francis Verpoort
α-Hydroxy ketones are a series of biologically active fragments in nature as well as important synthons for organic chemistry. Herein, an AgOAc/1-ethyl-3-methylimidazolium acetate ionic liquid system was developed for the CO2-promoted hydration of propargylic alcohols and H2O to produce α-hydroxy ketones. Diverse desired products could be obtained in satisfactory yields under 1 bar of CO2 pressure with the catalysis of only a trace amount of silver (0.005–0.25 mol %), which is the lowest level ever reported for the metal-catalyzed systems. In particular, this system had robust recyclability, and it could be reused effectively at least 5 times. Furthermore, an unprecedented turnover number (TON) of 9200 was achieved, which is considered to be the highest TON ever reached for this hydration.
研究领域:
有机化学
·
催化
·
绿色化学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF CATALYSIS
·
2021
·
IF 7.92
Ye Yuan,Jia Hu,Yu Wang,Leilei Huang,Jiayun Zheng,Yufeng Zhao,Yiyun Chen,Cheng Chen,Francis Verpoort
α-Hydroxy ketones are important building blocks in biological, pharmaceutical and synthetic chemistry. In this work, diverse α-hydroxy ketones were efficiently constructed through the CO 2 -promoted hydration process of propargyl alcohols, which was catalyzed by a system consisted of economical CuSO 4 ·5H 2 O and a green 1-butyl-3-methylimidazolium acetate ionic liquid. Particularly, this catalytic system exhibited excellent activity under atmospheric CO 2 or even mimetic flue gas (20 vol% of CO 2 ). Moreover, this system employed the lowest metal loading ever reported (0.004–0.25 mol%) meanwhile reached the highest turnover number (11700) for the target hydration reaction. Additionally, this is the first reported Cu catalytic system with reliable recyclability, which could be easily reused at least 6 times with yields higher than 85%.
研究领域:
催化
·
绿色化学
·
有机合成
✓ 已验证
DOI
高影响因子
Journal of CO2 Utilization
·
2018
·
IF 5.503
Dandan Song,Di Li,Xuan Xiao,Chen Cheng,Somboon Chaemchuen,Ye Yuan,Francis Verpoort
A green and recyclable catalytic system based on AgBr and an ionic liquid (IL) was developed for the three-component coupling reaction of propargylic alcohols, secondary amines and carbon dioxide (CO 2 ). A series of target carbamates, especially those generated from challenging substrates, could be obtained smoothly at atmospheric CO 2 pressure in a straightforward one-pot process. Moreover, the catalyst loading reached the lowermost level ever reported. Particularly, this catalytic system exhibited robust constancy and could be reused at least 5 times with retention of high catalytic activity. It is worth noting that this is the first catalytic system which could be recycled successfully for this reaction.
研究领域:
化学
·
催化
·
绿色化学
·
有机合成
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）