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镍催化的烯烃三组分1,2-碳酰化反应

Nickel-Catalyzed Three-Component 1,2-Carboacylation of Alkenes.

作者信息

Jin Shengzhou, Wang Lanfen, Jia Yinggang, Ma Wenbo, Wang Dingyi

机构信息

Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, China.

College of Sciences, Northeastern University, Shenyang 110004, China.

出版信息

Molecules. 2024 Sep 10;29(18):4295. doi: 10.3390/molecules29184295.

DOI:10.3390/molecules29184295
PMID:39339290
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11433782/
Abstract

Ketones, prevalent in many biologically significant molecules, require the development of novel methods to synthesize these structures, which is a critical endeavor in organic synthesis. Transition metal catalysis has proven to be an effective method for synthesizing ketones. However, the scope of these substrates remains relatively limited, particularly due to their incompatibility with sensitive functional groups. Herein, we report a Ni-catalyzed three-component 1,2-carboacylation of alkenes, which activates secondary/tertiary alkyl bromides. This method offers significant advantages: simplicity of operation, ready availability of substrates, and broad substrate applicability. A series of experimental studies have helped clarify the key mechanistic pathways involved in this cascade reaction.

摘要

酮类化合物存在于许多具有重要生物学意义的分子中,因此需要开发新的方法来合成这些结构,这是有机合成中的一项关键任务。过渡金属催化已被证明是合成酮类化合物的有效方法。然而,这些底物的范围仍然相对有限,特别是因为它们与敏感官能团不兼容。在此,我们报道了一种镍催化的烯烃1,2-碳酰化三组分反应,该反应可活化仲/叔烷基溴。该方法具有显著优势:操作简单、底物易于获得且底物适用性广泛。一系列实验研究有助于阐明该串联反应中涉及的关键机理途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/6b4d0c3afc93/molecules-29-04295-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/ce579f72f0f0/molecules-29-04295-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/b48f203321ad/molecules-29-04295-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/824ee9365ac2/molecules-29-04295-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/85f4550853ae/molecules-29-04295-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/6b4d0c3afc93/molecules-29-04295-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/ce579f72f0f0/molecules-29-04295-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/b48f203321ad/molecules-29-04295-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/824ee9365ac2/molecules-29-04295-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/85f4550853ae/molecules-29-04295-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8f6e/11433782/6b4d0c3afc93/molecules-29-04295-sch005.jpg

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本文引用的文献

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Org Lett. 2023 Mar 17;25(10):1673-1677. doi: 10.1021/acs.orglett.3c00307. Epub 2023 Mar 7.
2
The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins.二苯甲酮氢原子转移(HAT)光催化与硅基自由基引发的交叉亲电试剂捕获(XAT)的合并实现了镍催化的交叉亲电试剂偶联以及烯烃的1,2-双碳官能团化反应。
ACS Catal. 2022 Sep 16;12(18):11216-11225. doi: 10.1021/acscatal.2c03805. Epub 2022 Sep 1.
3
Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes.
镍催化烯烃分子间双碳官能化的最新进展
Chem Sci. 2020 Mar 6;11(17):4287-4296. doi: 10.1039/c9sc06006e.
4
Nickel-catalyzed three-component olefin reductive dicarbofunctionalization to access alkylborates.镍催化的三组分烯烃还原双碳官能化反应以制备硼酸烷基酯。
Chem Sci. 2020 Jul 8;11(30):7950-7956. doi: 10.1039/d0sc02054k.
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Nickel-Catalyzed Three-Component Reductive Alkylacylation of Electron-Deficient Activated Alkenes.镍催化缺电子活性烯烃的三组分还原烷基酰化反应
Org Lett. 2020 Nov 20;22(22):8829-8835. doi: 10.1021/acs.orglett.0c03210. Epub 2020 Oct 29.
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trans-Selective Aryldifluoroalkylation of Endocyclic Enecarbamates and Enamides by Nickel Catalysis.镍催化中环烯酰胺和烯酰胺的反选择性芳基二氟烷基化反应。
Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18741-18747. doi: 10.1002/anie.202008498. Epub 2020 Aug 24.
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J Am Chem Soc. 2020 Aug 5;142(31):13515-13522. doi: 10.1021/jacs.0c05254. Epub 2020 Jul 22.
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J Am Chem Soc. 2020 May 27;142(21):9604-9611. doi: 10.1021/jacs.0c03708. Epub 2020 May 14.
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