Amine-catalyzed site- and stereo-selective coupling of epoxy amines and carbon dioxide to construct oxazolidinones

Qiu, Wenqin; Jin, Feng; Hao, Yanhong; Bao, Xiaoguang; Yuan, Dan; Yao, Yingming

doi:10.1039/d2qo00583b

Cited by 7 publications

(2 citation statements)

References 42 publications

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“…Recently, an example of the organic amine-catalyzed selective coupling of epoxy amines and CO 2 to construct oxazolidinones is described under the atmospheric pressure of CO 2 . 137 Without using any metal and halide species, the tertiary amine can act as a nucleophile to successfully facilitate the ring-opening of the epoxides in the process.…”

Section: Organocatalysis and Activation In Co2 Conversionmentioning

confidence: 99%

Recent progress in CO₂ conversion into organic chemicals by molecular catalysis

Song¹,

Ma²,

Liu³

et al. 2023

Green Chem.

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Section: Organocatalysis and Activation In Co2 Conversionmentioning

confidence: 99%

Recent progress in CO₂ conversion into organic chemicals by molecular catalysis

Song¹,

Ma²,

Liu³

et al. 2023

Green Chem.

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“…, Al, − Ca, − and Ga), transition metals ( e.g. , Cr, , Fe, , Co, − and Zn − ), rare-earth metal complexes, − and organocatalysts. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Aluminum Complexes Stabilized by Amine-Bridged Tris(phenolato) Ligands and Their Applications in the Cycloaddition Reaction of CO₂ and Epoxides

Qing,

Tan,

Zhang

et al. 2023

Organometallics

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A series of amine-bridged tris(phenolato) aluminum complexes L 1 Al-L 7 Al (1−7) were synthesized through alkane elimination reactions of amino-bridged tris(phenol)s (L 1 Al-L 7 Al) with AlMe 3 . Complexes 1−7 were characterized through NMR, Xray diffraction analysis, and elemental analysis. Their catalytic activities in the cycloaddition reaction of CO 2 and epoxides were studied. The chloro-substituted o-phenylenediamine-bridged tris-(phenolato) aluminum complex 7 exhibited the highest catalytic activity. Under the conditions of 1 bar CO 2 and 85 °C, complex 7/ TBAB catalyzed the reaction of 15 monosubstituted epoxides with CO 2 , generating cyclic carbonates in 52−99% yields. Disubstituted epoxides were also transformed into cyclic carbonates in 60−99% yields in the presence of 10 bar CO 2 . Kinetic study of the cycloaddition of epichlorohydrin (ECH) and CO 2 revealed a zero-order dependence on CO 2 pressure and first-order dependence on the concentrations of ECH, complex 7, and TBAB.

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Exploring Cu(triNHC) as a Bifunctional Catalyst for Carbonate Synthesis From CO₂ and Epoxy Amines/Sulfides/Ethers

Ha,

Lee,

Sokolova

et al. 2024

Applied Organom Chemis

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This study highlights the synergistic interplay between a Lewis acidic copper ion and a dissociated ligand from Cu(triNHC) complexes in the synthesis of cyclic carbonates from CO2 and epoxy compounds. The reactions were found to proceed efficiently under Cu(triNHC)‐catalyzed conditions, yielding significant quantities of cyclic carbonates across various epoxy substrates encompassing amine, sulfide, and ether functionalities. Stereochemical analyses underscore a pronounced propensity for retaining the stereochemistry of epoxy compounds in the resultant carbonates. This suggests a mechanism involving double inversion of stereochemistry during the reaction, which comprises catalyst‐mediated epoxide ring opening, subsequent CO2 addition, and carbonate ring closing. These findings align with established mechanisms for CO2 fixation reactions, shedding light on the intricate pathways underlying this catalytic process.

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Amine-catalyzed site- and stereo-selective coupling of epoxy amines and carbon dioxide to construct oxazolidinones

Abstract: A non-metal catalyzed coupling of epoxy amine and CO2 was achieved using readily available tertiary amines, under atmospheric pressure of CO2 in the absence of any co-catalyst or additive. High...

Cited by 7 publications

References 42 publications

Recent progress in CO₂ conversion into organic chemicals by molecular catalysis

Recent progress in CO₂ conversion into organic chemicals by molecular catalysis

Synthesis of Aluminum Complexes Stabilized by Amine-Bridged Tris(phenolato) Ligands and Their Applications in the Cycloaddition Reaction of CO₂ and Epoxides

Exploring Cu(triNHC) as a Bifunctional Catalyst for Carbonate Synthesis From CO₂ and Epoxy Amines/Sulfides/Ethers

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Amine-catalyzed site- and stereo-selective coupling of epoxy amines and carbon dioxide to construct oxazolidinones

Abstract: A non-metal catalyzed coupling of epoxy amine and CO2 was achieved using readily available tertiary amines, under atmospheric pressure of CO2 in the absence of any co-catalyst or additive. High...

Cited by 7 publications

References 42 publications

Recent progress in CO2 conversion into organic chemicals by molecular catalysis

Recent progress in CO2 conversion into organic chemicals by molecular catalysis

Synthesis of Aluminum Complexes Stabilized by Amine-Bridged Tris(phenolato) Ligands and Their Applications in the Cycloaddition Reaction of CO2 and Epoxides

Exploring Cu(triNHC) as a Bifunctional Catalyst for Carbonate Synthesis From CO2 and Epoxy Amines/Sulfides/Ethers

Contact Info

Product

Resources

About

Recent progress in CO₂ conversion into organic chemicals by molecular catalysis

Recent progress in CO₂ conversion into organic chemicals by molecular catalysis

Synthesis of Aluminum Complexes Stabilized by Amine-Bridged Tris(phenolato) Ligands and Their Applications in the Cycloaddition Reaction of CO₂ and Epoxides

Exploring Cu(triNHC) as a Bifunctional Catalyst for Carbonate Synthesis From CO₂ and Epoxy Amines/Sulfides/Ethers