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新型吲哚基-杂环卡宾铜配合物的开发及其在催化中的应用。

Development of New Indole-Based -Heterocyclic Carbene Copper Complexes and Their Applications in Catalysis.

作者信息

Lin Chun-Fa, Tseng Ya-Hsuan, Hsieh Hui-Yu, Hung Pei-Jei, Huang Yan-Wen, Lee Dong-Sheng, Lu Ta-Jung

机构信息

Department of Chemistry, National Chung Hsing University, Taichung 40227, Taiwan.

出版信息

J Org Chem. 2025 Jun 6;90(22):7236-7245. doi: 10.1021/acs.joc.5c00248. Epub 2025 May 28.

DOI:10.1021/acs.joc.5c00248
PMID:40435294
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12150340/
Abstract

This study disclosed the synthesis and characterization of a series of copper -heterocyclic carbene (NHC) complexes incorporating an indole skeleton. Among these complexes, the Cu-NHC complex with a -methoxyphenyl group on the indole ring exhibited stability in air for up to six months. In contrast, Cu-NHC complexes bearing alkyl groups on the indole ring were stable under a nitrogen atmosphere for one month. These newly developed Cu-NHC complexes proved effective as catalysts for hydrosilylation of carbonyls in 0.5 mol % loading and -arylation of oxazolidinones and amides with aryl iodides in 8 mol % loading.

摘要

本研究揭示了一系列含有吲哚骨架的铜-杂环卡宾（NHC）配合物的合成与表征。在这些配合物中，吲哚环上带有对甲氧基苯基的铜-NHC配合物在空气中可稳定存在长达六个月。相比之下，吲哚环上带有烷基的铜-NHC配合物在氮气气氛下可稳定一个月。这些新开发的铜-NHC配合物被证明是有效的催化剂，用于羰基的硅氢化反应（负载量为0.5 mol%）以及恶唑烷酮和酰胺与芳基碘的芳基化反应（负载量为8 mol%）。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/9bc920638335/jo5c00248_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/783a9fd8fd64/jo5c00248_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/e7c19943cd88/jo5c00248_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/75e5074ce625/jo5c00248_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/601e5d83e396/jo5c00248_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/9bc920638335/jo5c00248_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/783a9fd8fd64/jo5c00248_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/e7c19943cd88/jo5c00248_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/75e5074ce625/jo5c00248_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/601e5d83e396/jo5c00248_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2526/12150340/9bc920638335/jo5c00248_0003.jpg

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本文引用的文献

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J Org Chem. 2024 Jul 5;89(13):9322-9335. doi: 10.1021/acs.joc.4c00418. Epub 2024 Jun 21.
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Room Temperature Cu-Catalyzed -Arylation of Oxazolidinones and Amides with (Hetero)Aryl Iodides.室温下 Cu 催化的恶唑烷酮和酰胺与（杂）芳基碘的 -芳基化反应。
Org Lett. 2022 Feb 11;24(5):1253-1257. doi: 10.1021/acs.orglett.2c00122. Epub 2022 Jan 31.
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An indole-amide-based phosphine ligand enabling a general palladium-catalyzed sterically hindered Suzuki-Miyaura cross-coupling reaction.
一种基于吲哚酰胺的膦配体，能够实现通用的钯催化的空间位阻铃木-宫浦交叉偶联反应。
Org Biomol Chem. 2022 Feb 16;20(7):1373-1378. doi: 10.1039/d1ob02294f.
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Chemoselective Copper-Catalyzed Ullmann-Type Coupling of Oxazolidinones with Bromoiodoarenes.铜催化的恶唑烷酮与溴碘芳烃的 Chemoselective Ullmann 型偶联反应。
Org Lett. 2017 Jun 2;19(11):3021-3024. doi: 10.1021/acs.orglett.7b01304. Epub 2017 May 22.
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Alkylfluorenyl substituted N-heterocyclic carbenes in copper(I) catalysed hydrosilylation of aldehydes and ketones.烷基芴基取代的N-杂环卡宾在铜（I）催化的醛和酮的硅氢化反应中的应用
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