C2-symmetric metalloporphyrin promoted cycloaddition of epoxides with CO2 under atmospheric pressure

Jiang, Xu; Gou, Faliang; Qi, Chenze

doi:10.1016/j.jcou.2018.12.003

Cited by 29 publications

(11 citation statements)

References 51 publications

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“…In this respect, many catalysts have been synthesized and exhibited a good performance in the synthesis of cyclic carbonates from CO2. Metal−based catalysts including metal-organic framework (MOF), 54,55 metal (salen) complex 56,57 and metal-porphyrins [58][59][60] were reported to have a good yield of cyclic carbonates at atmospheric pressure and/or room temperature for the activity sites of metal ions and halide ions. For example, North and coworkers reported an Cr(III) salphen complexes for the cycloaddition reaction under ambient conditions with the presence of TBAB (tetrabutylammonium bromide).…”

Section: Introductionmentioning

confidence: 99%

Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

et al. 2019

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“…The resulting cyclic carbonates are widely used as intermediates, aprotic polar solvents, electrolytes in lithium ion batteries, raw materials, and fuel additives etc . Recent communications show that metalloporphyrins work cooperatively with quaternary ammonium salts for the cycloaddition of epoxides and CO 2 to produce cyclic carbonates . In particular, the ammonium‐functionalized metalloporphyrins with suitable anions have attracted growing attention.…”

Section: Introductionmentioning

confidence: 99%

Cycloaddition Reactions of Epoxides and CO₂ by the Novel Imidazolium‐Functionalized Metalloporphyrins: Optimization and Analysis using Response Surface Methodology

et al. 2020

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The production of cyclic carbonates using CO 2 and epoxides has received great attention due to 100 % atom utilization. Herein, novel imidazolium-containing metalloporphyrins were synthesized as bifunctional catalysts for the cycloaddition reactions of epoxides and CO 2. The reaction conditions were optimized and analyzed with the response surface methodology. Under the optimum condition using Zn-porphyrin 1 as the catalyst, the turnover number (TON) and turnover number frequency (TOF) for the cycloaddition of CO 2 and ECH were 11,629 and 1,735, respectively. In addition, analysis of the RSM indicated that the CO 2 pressure had only a small impact on the yield. Based on this conclusion, the catalytic activity of 1 was further evaluated under mild conditions. Regardless of whether the CO 2 pressure is high or ambient, this Zn-porphyrin exhibited an excellent performance with a high turnover number frequency.

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“…Several mechanistic studies have been carried out with metalloporphyrins as Lewis acid catalysts associated to nucleophilic anions from ammonium salts or to N‐heterocyclic bases (DMAP, N‐methylimidazole, pyridine) forming either two‐component or bifunctional single‐component catalysts [6d,11e,18c,e,h,26] . The generally accepted mechanism involves activation of the epoxide through coordination to the metal centre followed by ring‐opening by nucleophilic attack on the less hindered epoxide carbon atom.…”

Section: Resultsmentioning

confidence: 99%

A flexible bis‐Co(III) porphyrin cage as a bimetallic catalyst for the conversion of CO₂ and epoxides into cyclic carbonates

et al. 2020

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A molecular cage consisting of two free-base porphyrins connected by four flexible linkers was metalated with Co(III) to afford in good yield a bimetallic catalyst. The catalytic activity of the bis-Co(III) porphyrin molecular cage (CoCl) 2-1 was studied for the formation of cyclic carbonates from CO 2 and propylene oxide (PO) or styrene oxide (SO) with pyridine as cocatalyst. Various reaction parameters such as the molar ratio of the catalyst and the co-catalyst, the time of reaction, the temperature and CO 2 pressure were investigated. The molecular cage was shown to be a catalyst of high selectivity for the studied reactions and much more efficient to convert the epoxides to the corresponding cyclic carbonates than the monomeric Co(III) Cl meso-tetraphenylporphyrin (CoCl-TPP) model. When quantitative conversion of PO into propylene carbonate (PC) was reached (0.1 mol% catalyst, 1.2 mol% pyridine, 120°C, 30 bar of CO 2) only 23 % of PC was obtained with CoCl-TPP (0.2 mol%). This enhanced catalytic activity is attributed to the synergistic effect of the two metal sites incorporated in the framework of the molecular cage.

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C2-symmetric metalloporphyrin promoted cycloaddition of epoxides with CO2 under atmospheric pressure

Cited by 29 publications

References 51 publications

Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

Cycloaddition Reactions of Epoxides and CO₂ by the Novel Imidazolium‐Functionalized Metalloporphyrins: Optimization and Analysis using Response Surface Methodology

A flexible bis‐Co(III) porphyrin cage as a bimetallic catalyst for the conversion of CO₂ and epoxides into cyclic carbonates

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C2-symmetric metalloporphyrin promoted cycloaddition of epoxides with CO2 under atmospheric pressure

Cited by 29 publications

References 51 publications

Efficient transformation of CO2 to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

Efficient transformation of CO2 to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

Cycloaddition Reactions of Epoxides and CO2 by the Novel Imidazolium‐Functionalized Metalloporphyrins: Optimization and Analysis using Response Surface Methodology

A flexible bis‐Co(III) porphyrin cage as a bimetallic catalyst for the conversion of CO2 and epoxides into cyclic carbonates

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Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

Efficient transformation of CO₂ to cyclic carbonates using bifunctional protic ionic liquids under mild conditions

Cycloaddition Reactions of Epoxides and CO₂ by the Novel Imidazolium‐Functionalized Metalloporphyrins: Optimization and Analysis using Response Surface Methodology

A flexible bis‐Co(III) porphyrin cage as a bimetallic catalyst for the conversion of CO₂ and epoxides into cyclic carbonates