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酯的有机催化合成路线及其在硅氢化反应过程中的应用。

Organocatalytic synthetic route to esters and their application in hydrosilylation process.

作者信息

Mermela Aleksandra, Bołt Małgorzata, Mrzygłód Aleksandra, Żak Patrycja

机构信息

Faculty of Chemistry, Department of Organometallic Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614, Poznań, Poland.

Centre for Advanced Technologies, Uniwersytetu Poznańskiego 10, 61-614, Poznań, Poland.

出版信息

Sci Rep. 2024 Aug 17;14(1):19108. doi: 10.1038/s41598-024-70036-y.

DOI:10.1038/s41598-024-70036-y
PMID:39154105
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11330490/
Abstract

A facile esterification of α,β-unsaturated aldehydes with alcohols has been developed for the synthesis of esters by using bulky N-heterocyclic (NHC) carbene as a metal-free and eco-friendly organocatalyst. This new protocol has been proved to be effective with a wide substrate scope, giving selective esters in yields greater than 84% under mild conditions. Moreover, proposed synthetic strategy enables modification of various types of silsesquioxanes (SQ) which cannot or are technically difficult to be carried out with known protocols. For the first time, a one-pot sequential esterification/hydrosilylation has been successfully carried out.

摘要

已开发出一种利用大位阻氮杂环（NHC）卡宾作为无金属且环保的有机催化剂，使α,β-不饱和醛与醇进行简便酯化反应来合成酯的方法。该新方案已被证明在广泛的底物范围内有效，在温和条件下能以大于84%的产率得到选择性酯。此外，所提出的合成策略能够对各种类型的倍半硅氧烷（SQ）进行修饰，而这是已知方法无法实现或在技术上难以进行的。首次成功实现了一锅法连续酯化/硅氢化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/8c5ee82d79c5/41598_2024_70036_Fig10_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/bcc96f00a30b/41598_2024_70036_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/9f143091550f/41598_2024_70036_Fig2_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/cb281b017fd1/41598_2024_70036_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/d83dd21656e1/41598_2024_70036_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/7079597dd1da/41598_2024_70036_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/76cde0c0ce94/41598_2024_70036_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f10e/11330490/8c5ee82d79c5/41598_2024_70036_Fig10_HTML.jpg

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本文引用的文献

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Materials (Basel). 2024 Jan 4;17(1):268. doi: 10.3390/ma17010268.
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Metal-free synthesis of unsymmetric bis(thioesters).无金属合成不对称双硫酯。
Chem Commun (Camb). 2023 Jan 19;59(7):956-959. doi: 10.1039/d2cc05160e.
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Use of Polyhedral Oligomeric Silsesquioxane (POSS) in Drug Delivery, Photodynamic Therapy and Bioimaging.多面体低聚倍半硅氧烷（POSS）在药物传递、光动力疗法和生物成像中的应用。
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Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now.N-杂环卡宾有机催化中的核心角色——布雷斯洛中间体的故事：过去与现在
Chem Sci. 2021 May 11;12(23):7973-7992. doi: 10.1039/d1sc01910d.
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Novel Polyhedral Silsesquioxanes [POSS(OH)] as Anthracycline Nanocarriers-Potential Anticancer Prodrugs.新型多面体倍半硅氧烷[POSS(OH)]作为阿霉素纳米载体-潜在的抗癌前药。
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Acyl Donor Intermediates in N-Heterocyclic Carbene Catalysis: Acyl Azolium or Azolium Enolate?N-杂环卡宾催化中的酰基供体中间体：酰基唑鎓盐还是烯醇化唑鎓盐？
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Chemoselective dehydrogenative esterification of aldehydes and alcohols with a dimeric rhodium(ii) catalyst.使用二聚铑（II）催化剂对醛和醇进行化学选择性脱氢酯化反应。
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