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钌-镍催化下酚类的机械化学顺序脱氧交叉偶联反应

Mechanochemical Sequential Deoxygenative Cross-Coupling Reactions of Phenols Under Ruthenium-Nickel Catalysis.

作者信息

Mkrtchyan Satenik, Purohit Vishal B, Jakubczyk Michał, Prajapati Vaibhav D, Prajapati Ronak V, Garcia Michael G, Karpun Eugene, Yepishev Vitaliy, Saini Manoj K, Sarfaraz Sehrish, Ayub Khurshid, Addová Gabriela, Filo Juraj, Iaroshenko Viktor O

机构信息

Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, Tajovskeho 40, 974 01 Banska Bystrica, Slovakia.

Department of Chemical Sciences, P. D. Patel Institute of Applied Sciences, Charotar University of Science and Technology (CHARUSAT), Changa 388421, Gujarat, India.

出版信息

Molecules. 2025 Apr 19;30(8):1835. doi: 10.3390/molecules30081835.

DOI:10.3390/molecules30081835
PMID:40333846
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12029765/
Abstract

Herein, we report the first mechanochemical strategy for the Ru-catalyzed deoxygenative borylation of free phenols via C-O bond cleavage. This Ru-catalyzed phenolic borylation approach has been successfully extended to the Suzuki-Miyaura-type cross-coupling of phenols with aryl bromides. The protocol accepts a wide scope of phenolic substrates, allowing the synthesis of aryl pinacolboranes and biphenyl structures in excellent yields and serving as a better alternative to classical cross-coupling reactions in the context of pot, atom, and step economy synthesis.

摘要

在此,我们报道了首例通过碳-氧键断裂实现钌催化游离酚脱氧硼化的机械化学策略。这种钌催化的酚硼化方法已成功扩展到酚与芳基溴的铃木-宫浦型交叉偶联反应。该方案适用于广泛的酚类底物,能够以优异的产率合成芳基频哪醇硼酸酯和联苯结构,并且在釜式、原子和步骤经济性合成方面是经典交叉偶联反应的更好替代方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/7008d012bea7/molecules-30-01835-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/e31ae62bea86/molecules-30-01835-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/13f92b447b2a/molecules-30-01835-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/ce76725ad5e4/molecules-30-01835-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/004d344d2c3b/molecules-30-01835-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/fd041089fca0/molecules-30-01835-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/7008d012bea7/molecules-30-01835-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/e31ae62bea86/molecules-30-01835-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/13f92b447b2a/molecules-30-01835-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/ce76725ad5e4/molecules-30-01835-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/004d344d2c3b/molecules-30-01835-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/fd041089fca0/molecules-30-01835-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/24ea/12029765/7008d012bea7/molecules-30-01835-g002.jpg

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本文引用的文献

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Mechanochemical synthesis of aromatic ketones: pyrylium tetrafluoroborate mediated deaminative arylation of amides.芳香酮的机械化学合成:四氟硼酸吡喃鎓介导的酰胺脱氨基芳基化反应
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Mechanochemistry Drives Alkene Difunctionalization via Radical Ligand Transfer and Electron Catalysis.机械化学通过自由基配体转移和电子催化驱动烯烃双官能化反应。
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Ruthenium/η-Phenoxo-Catalyzed Amination of Phenols with Amines.
钌/η-苯氧基催化酚类与胺类的胺化反应
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Mechanochemical arylative detrifluoromethylation of trifluoromethylarenes.三氟甲基芳烃的机械化学芳基化脱三氟甲基化反应
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Mechanochemical Defluorinative Arylation of Trifluoroacetamides: An Entry to Aromatic Amides.机械化学脱氟芳基化三氟乙酰胺:芳香酰胺的一种合成方法。
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