184007-11-2Relevant articles and documents
Preparation of Optically Active Cyclic Carbonates and 1,2-Diols via Enantioselective Hydrogenation of α-Methylenedioxolanones Catalyzed by Chiral Ruthenium(II) Complexes
Gendre, Pierre Le,Braun, Thomas,Bruneau, Christian,Dixneuf, Pierre H.
, p. 8453 - 8455 (1996)
The enantioselective hydrogenation of α-methylene-1,3-dioxolan-2-ones catalyzed by chiral (diphosphine)ruthenium complexes leads to optically active cyclic carbonates with high enantioselectivities.Their hydrolysis in methanol in the presence of potassium carbonate quantitatively affords optically active 1,2-diols.
Bifunctional silver(I) complex-catalyzed CO2 conversion at ambient conditions: Synthesis of α-methylene cyclic carbonates and derivatives
Song, Qing-Wen,Chen, Wei-Qiang,Ma, Ran,Yu, Ao,Li, Qiu-Yue,Chang, Yao,He, Liang-Nian
, p. 821 - 827 (2015)
Abstract The chemical conversion of CO2 at atmospheric pressure and room temperature remains a great challenge. The triphenylphosphine complex of silver(I) carbonate was proved to be a robust bifunctional catalyst for the carboxylative cyclization of propargylic alcohols and CO2 at ambient conditions leading to the formation of α-methylene cyclic carbonates in excellent yields. The unprecedented performance of [(PPh3)2Ag]2CO3 is presumably attributed to the simultaneous activation of CO2 and propargylic alcohol. Moreover, the highly compatible basicity of the catalytic species allows propargylic alcohol to react with CO2 leading to key silver alkylcarbonate intermediates: the bulkier [(Ph3P)2AgI]+ effectively activates the carbon-carbon triple bond and enhances O-nucleophilicity of the alkylcarbonic anion, thereby greatly promoting the intramolecular nucleophilic cyclization. Notably, this catalytic protocol also worked well for the reaction of propargylic alcohols, secondary amines, and CO2 (at atmospheric pressure) to afford β-oxopropylcarbamates.
Highly efficient synthesis of alkylidene cyclic carbonates from low concentration CO2using hydroxyl and azolate dual functionalized ionic liquids
Shi, Guiling,Zhai, Ran,Li, Haoran,Wang, Congmin
, p. 592 - 596 (2021)
A highly efficient catalytic system was developed for the reaction between CO2 and propargylic alcohols for alkylidene cyclic carbonates. Ionic liquids (ILs) with different anions and cations were designed as cocatalysts, in order to find out the effect of the cation and the anion on this reaction. The results indicated that the effect of the cation was significant, especially the hydroxyl group on the cation played an important role due to the presence of a hydrogen bond. It was also found that the basicity of the anion was important for its catalytic activity, where the anion with moderate basicity gave the best activity. Moreover, this hydroxyl and azolate dual functionalized catalytic system showed excellent reusability and generality. It is worth mentioning that at a low concentration of CO2, this dual functionalized catalytic system showed excellent catalytic activity even in a gram-scale reaction, indicating its potential in carbon capture and utilization processes.
Reusable polymer-supported amine-copper catalyst for the formation of α-alkylidene cyclic carbonates in supercritical carbon dioxide
Jiang, Huan-Feng,Wang, A.-Zhong,Liu, Hai-Ling,Qi, Chao-Rong
, p. 2309 - 2312 (2008)
A green, simple and effective polymer-supported catalytic system has been developed for the cyclization of propargyl alcohols with carbon dioxide (CO 2). α-Alkylidene cyclic carbonates were obtained in satisfactory isolated yields in most cases. The catalyst could be recovered by simple filtration and reused several times without significant loss of activity. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Copper-catalysed synthesis of α-alkylidene cyclic carbonates from propargylic alcohols and CO2
Cervantes-Reyes, Alejandro,Farshadfar, Kaveh,Rudolph, Matthias,Rominger, Frank,Schaub, Thomas,Ariafard, Alireza,Hashmi
supporting information, p. 889 - 897 (2021/02/09)
We report a N-heterocyclic carbene copper(i) complex-catalysed formal cycloaddition between readily available propargylic alcohols and carbon dioxide at room temperature. By using the combination of a sterically demandingBPDPrCuCl complex (BPDPr = 1,3-bis(2,6-diisopropylphenyl)-1,3-diazonine-2-ylidene) and CsF, as catalytic system, primary propargylic alcohols are efficiently converted to the corresponding α-alkylidene cyclic carbonates. Gram scale (up to 89% yield) and reusability experiments (74% global yield, turnover number value = 103) showcase the robustness of the catalytic system. This practically simple protocol also tolerates secondary and tertiary propargylic alcohols under CO2at atmospheric pressure, enabling the direct synthesis of substituted and unsubstituted α-alkylidene cyclic carbonates at room temperature.
A dual-functional urea-linked conjugated porous polymer anchoring silver nanoparticles for highly efficient CO2conversion under mild conditions
Li, Lin,Li, Wang,Li, Yuting,Liu, Xiaozhen,Wang, Jianxin,Wang, Liping,Wang, Xiaoji,Zhu, Jie
, p. 13052 - 13059 (2020/10/13)
A dual-functional urea-linked conjugated porous polymer (UCPP) assembled by enol-imine with ordered unit arrays that act as potential anchoring sites in the networks was fabricated, and was further applied as a support for Ag nanoparticles by the coordinate interaction between them. The UCPP not only can well confine the Ag particle size and facilitate high dispersion, but also can afford special CO2-philic moieties to enhance the adsorption properties. The resulting Ag?UCPP as a heterogeneous catalyst exhibited excellent activity for the carboxylative cyclization of propargyl alcohols with CO2 under mild conditions, together with good recyclability, which is probably attributed to the synergistic effect of the UCPP on the adsorption and activation of CO2 and the immobilization of Ag nanoparticles. This work affords possible opportunities for the design and synthesis of a heterogeneous catalyst toward CO2 conversion.
