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钯催化的可见光条件下 4CzIPN 介导的 O-甲基酮肟与α-酮酸的脱羧酰化反应。

A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light.

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China.

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453000, China.

出版信息

Molecules. 2022 Mar 18;27(6):1980. doi: 10.3390/molecules27061980.

DOI:10.3390/molecules27061980
PMID:35335341
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8955727/
Abstract

This work presents a palladium-catalyzed oxime ether-directed ortho-selective benzoylation using benzoylformic acid as the acyl source with a palladium catalyst and 4CzIPN as the co-catalyst under light. Various non-symmetric benzophenone derivatives were obtained in moderate to good yields. A preliminary mechanism study revealed that the reaction proceeds through a free radical pathway.

摘要

本文提出了一种钯催化的肟醚导向的邻位选择性苯甲酰化反应,使用苯甲酰甲酸作为酰基源,钯催化剂和 4CzIPN 作为共催化剂,并在光照下进行。各种非对称二苯甲酮衍生物都以中等至良好的产率得到。初步的机理研究表明,反应是通过自由基途径进行的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/fe538efc8f4b/molecules-27-01980-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/217af7adc863/molecules-27-01980-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/44b5e595816e/molecules-27-01980-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/1a6a168128ad/molecules-27-01980-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/a306f9710dd5/molecules-27-01980-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/055b58cf20ee/molecules-27-01980-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/fe538efc8f4b/molecules-27-01980-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/217af7adc863/molecules-27-01980-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/44b5e595816e/molecules-27-01980-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/1a6a168128ad/molecules-27-01980-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/a306f9710dd5/molecules-27-01980-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/055b58cf20ee/molecules-27-01980-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0d0b/8955727/fe538efc8f4b/molecules-27-01980-sch005.jpg

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本文引用的文献

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Rhodium(III)-Catalyzed Oxidative Annulation of Ketoximes with Sulfonamide: A Direct Approach to Indazoles.铑(III)催化酮肟与磺酰胺的氧化环化反应:一种直接合成吲唑的方法。
Org Lett. 2019 Jan 18;21(2):365-368. doi: 10.1021/acs.orglett.8b03488. Epub 2019 Jan 8.
2
Bioinspired Radical Stetter Reaction: Radical Umpolung Enabled by Ion-Pair Photocatalysis.受生物启发的自由基斯特特勒反应:离子对光催化引发的自由基反转。
Angew Chem Int Ed Engl. 2019 Jan 21;58(4):1208-1212. doi: 10.1002/anie.201809601. Epub 2018 Dec 12.
3
Ruthenium(II)-Catalyzed C-H Difluoromethylation of Ketoximes: Tuning the Regioselectivity from the meta to the para Position.
钌(II)催化的酮肟的 C-H 二氟甲基化反应:调节区域选择性从间位到对位。
Angew Chem Int Ed Engl. 2018 Jan 26;57(5):1277-1281. doi: 10.1002/anie.201711221. Epub 2018 Jan 2.
4
Palladium-catalyzed decarboxylative, decarbonylative and dehydrogenative C(sp)-H acylation at room temperature.钯催化的室温下脱羧、脱羰和脱氢的C(sp)-H酰化反应
Org Biomol Chem. 2017 Aug 9;15(31):6592-6603. doi: 10.1039/c7ob01466j.
5
Pd(II)-Catalyzed Direct ortho-C-H Acylation of Aromatic Ketones by Oxidative Decarboxylation of α-Oxocarboxylic Acids.Pd(II) 催化的芳香酮的直接邻位 C-H 酰化反应通过α-氧代羧酸的氧化脱羧实现。
Org Lett. 2017 Apr 21;19(8):2082-2085. doi: 10.1021/acs.orglett.7b00677. Epub 2017 Apr 4.
6
Merging Visible-Light Photocatalysis and Palladium Catalysis for C-H Acylation of Azo- and Azoxybenzenes with α-Keto Acids.可见光光催化与钯催化相结合用于偶氮苯和氧化偶氮苯与α-酮酸的C-H酰化反应
Chemistry. 2016 Feb 12;22(7):2236-42. doi: 10.1002/chem.201504530. Epub 2016 Jan 7.
7
Merging Photoredox with Palladium Catalysis: Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids under Mild Reaction Conditions.光氧化还原与钯催化协同作用:温和反应条件下α-氧代羧酸对乙酰苯胺的脱羧邻位酰化反应。
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Combining rhodium and photoredox catalysis for C-H functionalizations of arenes: oxidative Heck reactions with visible light.铑和光氧化还原催化在芳环 C-H 官能化中的结合:可见光促进的氧化 Heck 反应。
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