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

IF 1.7 4区 化学
Jieun Lee, Wooram Lee, Yoseph Kim, Mujin Choi, Seol Ryu, Joonkyung Jang, Youngjo Kim
{"title":"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","authors":"Jieun Lee,&nbsp;Wooram Lee,&nbsp;Yoseph Kim,&nbsp;Mujin Choi,&nbsp;Seol Ryu,&nbsp;Joonkyung Jang,&nbsp;Youngjo Kim","doi":"10.1002/bkcs.12901","DOIUrl":null,"url":null,"abstract":"<p>We used stable and nontoxic [(dimethylamino)methyl]ferrocene (<b>Fc-N</b>), (hydroxymethyl)ferrocene (<b>Fc-O</b>), 1,2-bis[(dimethylamino)methyl]ferrocene (<b>Fc-N2</b>), and 1-[(dimethylamino)methyl]-2-(hydroxymethyl)ferrocene (<b>Fc-NO</b>) 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, <b>Fc-N2</b> exhibited the best catalytic activity under the same reaction conditions. Catalytic activity decreased rapidly in the order <b>Fc-N2</b> &gt; <b>Fc-NO</b> &gt; <b>Fc-N</b> &gt; <b>Fc-O</b>, 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.</p>","PeriodicalId":54252,"journal":{"name":"Bulletin of the Korean Chemical Society","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and computational studies for halide-free, neutral, and bifunctional one-component ferrocene-based catalysts for the coupling of carbon dioxide and epoxides\",\"authors\":\"Jieun Lee,&nbsp;Wooram Lee,&nbsp;Yoseph Kim,&nbsp;Mujin Choi,&nbsp;Seol Ryu,&nbsp;Joonkyung Jang,&nbsp;Youngjo Kim\",\"doi\":\"10.1002/bkcs.12901\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>We used stable and nontoxic [(dimethylamino)methyl]ferrocene (<b>Fc-N</b>), (hydroxymethyl)ferrocene (<b>Fc-O</b>), 1,2-bis[(dimethylamino)methyl]ferrocene (<b>Fc-N2</b>), and 1-[(dimethylamino)methyl]-2-(hydroxymethyl)ferrocene (<b>Fc-NO</b>) 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, <b>Fc-N2</b> exhibited the best catalytic activity under the same reaction conditions. Catalytic activity decreased rapidly in the order <b>Fc-N2</b> &gt; <b>Fc-NO</b> &gt; <b>Fc-N</b> &gt; <b>Fc-O</b>, 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.</p>\",\"PeriodicalId\":54252,\"journal\":{\"name\":\"Bulletin of the Korean Chemical Society\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-09-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bulletin of the Korean Chemical Society\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/bkcs.12901\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bulletin of the Korean Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/bkcs.12901","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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

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

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.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信