Synthesis and computational studies for halide-free, neutral, and bifunctional one-component ferrocene-based catalysts for the coupling of carbon dioxide and epoxides

IF 1.7 4区 化学 Bulletin of the Korean Chemical Society Pub Date : 2024-09-26 DOI:10.1002/bkcs.12901
Jieun Lee, Wooram Lee, Yoseph Kim, Mujin Choi, Seol Ryu, Joonkyung Jang, Youngjo Kim
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Abstract

We used stable and nontoxic [(dimethylamino)methyl]ferrocene (Fc-N), (hydroxymethyl)ferrocene (Fc-O), 1,2-bis[(dimethylamino)methyl]ferrocene (Fc-N2), and 1-[(dimethylamino)methyl]-2-(hydroxymethyl)ferrocene (Fc-NO) as halide-free, neutral, and bifunctional one-component catalysts for the synthesis of cyclic carbonates. They do not need halide-based additives or tethered salts attached to ligands when used for this coupling reaction. Among them, Fc-N2 exhibited the best catalytic activity under the same reaction conditions. Catalytic activity decreased rapidly in the order Fc-N2 > Fc-NO > Fc-N > Fc-O, and interestingly, the more amino groups introduced into the Cp groups, the higher the activity. Various terminal and internal epoxides were easily converted into the corresponding cyclic carbonates. Calculations based on the density functional theory were also carried out to elucidate the mechanism of the coupling reaction.

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用于二氧化碳与环氧化物偶联的无卤、中性和双功能单组分二茂铁基催化剂的合成与计算研究
我们使用稳定无毒的[(二甲基氨基)甲基]二茂铁(Fc-N)、(羟甲基)二茂铁(Fc-O)、1,2-双[(二甲基氨基)甲基]二茂铁(Fc-N2)和 1-[(二甲基氨基)甲基]-2-(羟甲基)二茂铁(Fc-NO)作为无卤、中性和双官能的单组分催化剂,用于合成环状碳酸盐。用于该偶联反应时,它们不需要卤基添加剂或配体上附带的系盐。在相同的反应条件下,Fc-N2 的催化活性最好。催化活性按照 Fc-N2 > Fc-NO > Fc-N > Fc-O 的顺序迅速降低,有趣的是,在 Cp 基团中引入的氨基越多,活性越高。各种末端和内部环氧化物很容易转化成相应的环碳酸盐。研究人员还根据密度泛函理论进行了计算,以阐明偶联反应的机理。
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来源期刊
Bulletin of the Korean Chemical Society
Bulletin of the Korean Chemical Society Chemistry-General Chemistry
自引率
23.50%
发文量
182
期刊介绍: The Bulletin of the Korean Chemical Society is an official research journal of the Korean Chemical Society. It was founded in 1980 and reaches out to the chemical community worldwide. It is strictly peer-reviewed and welcomes Accounts, Communications, Articles, and Notes written in English. The scope of the journal covers all major areas of chemistry: analytical chemistry, electrochemistry, industrial chemistry, inorganic chemistry, life-science chemistry, macromolecular chemistry, organic synthesis, non-synthetic organic chemistry, physical chemistry, and materials chemistry.
期刊最新文献
Masthead Cover Picture: Synthesis and computational studies for halide-free, neutral, and bifunctional one-component ferrocene-based catalysts for the coupling of carbon dioxide and epoxides (BKCS 10/2024) Jieun Lee, Wooram Lee, Yoseph Kim, Mujin Choi, Seol Ryu, Joonkyung Jang, Youngjo Kim Cost-effective synthesis of unsymmetric tetrazines Moisture-resistant nitroaromatic explosive gas sensor based on hydrophilic pentiptycene polymer Synthesis and computational studies for halide-free, neutral, and bifunctional one-component ferrocene-based catalysts for the coupling of carbon dioxide and epoxides
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