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通过能量转移过程实现的可见光介导的1,2-二羰基化合物的脱氧转化。

Visible-light-mediated deoxygenative transformation of 1,2-dicarbonyl compounds through energy transfer process.

作者信息

Luo Yun-Xuan, Huang Jie, Wu Guojiao, Tang Xiang-Ying, Qu Jin-Ping

机构信息

Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), Wuhan, People's Republic of China.

Guangdong Provincial Key Laboratory of Technique and Equipment for Macromolecular Advanced Manufacturing, South China University of Technology, Guangzhou, Guangdong, People's Republic of China.

出版信息

Nat Commun. 2024 Oct 25;15(1):9240. doi: 10.1038/s41467-024-53635-1.

DOI:10.1038/s41467-024-53635-1
PMID:39455565
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11511947/
Abstract

Through the energy transfer process, mild transformations can be achieved that are often difficult to realize under thermodynamic conditions. Herein, a visible-light-driven deoxygenative coupling of 1,2-dicarbonyl compounds for C-O, C-S, and C-N bonds construction is developed via triplet state 1,2-dicarbonyls, affording a wide range of α-functionalized ketones/esters under transition-metal and external photocatalyst free conditions. The usefulness of this method is demonstrated by gram-scale synthesis, late-stage functionalization of various carboxylic acid drugs, and the synthesis of natural products and drug molecules.

摘要

通过能量转移过程，可以实现温和的转化，而这些转化在热力学条件下往往难以实现。在此，通过三重态1,2-二羰基化合物开发了一种用于构建C-O、C-S和C-N键的可见光驱动的1,2-二羰基化合物脱氧偶联反应，在无过渡金属和外部光催化剂的条件下得到了多种α-官能化酮/酯。克级规模合成、各种羧酸药物的后期官能化以及天然产物和药物分子的合成证明了该方法的实用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/56bde0e1d4ef/41467_2024_53635_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/f2c6f8d185d1/41467_2024_53635_Fig1_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/d7995101139e/41467_2024_53635_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/5657785eae89/41467_2024_53635_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/456c487273d2/41467_2024_53635_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/56bde0e1d4ef/41467_2024_53635_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/f2c6f8d185d1/41467_2024_53635_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/d8b3ffb8549f/41467_2024_53635_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/ba9de3a7b575/41467_2024_53635_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/d7995101139e/41467_2024_53635_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/5657785eae89/41467_2024_53635_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/456c487273d2/41467_2024_53635_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dac5/11511947/56bde0e1d4ef/41467_2024_53635_Fig7_HTML.jpg

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本文引用的文献

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Catalytic Intermolecular Deoxygenative Coupling of Carbonyl Compounds with Alkynes by a Cp*Mo(II)-Catalyst.通过 Cp*Mo(II) 催化剂实现羰基化合物与炔烃的催化分子间脱氧偶联反应。
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Energy transfer photocatalysis: exciting modes of reactivity.
能量转移光催化：激发反应模式
Chem Soc Rev. 2024 Feb 5;53(3):1068-1089. doi: 10.1039/d3cs00190c.
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Regioselective Hydrodeoxygenation of α-Diketones with Phosphites under Visible-Light Catalysis.可见光催化下亚磷酸酯对α-二酮的区域选择性加氢脱氧反应
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