Reactivity and mechanistic insight into the cross coupling reaction between isochromans and β-keto esters through C–H bond activation under visible light irradiation

文献情報

出版日 2016-02-10

DOI 10.1039/C5QO00412H

インパクトファクター 5.281

著者

Ming Xiang, Qing-Yuan Meng, Xue-Wang Gao, Tao Lei, Bin Chen, Chen-Ho Tung, Li-Zhu Wu

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要旨

The visible light catalytic cross coupling reaction from two different C–H bonds provides an efficient protocol for C–H bond activation and C–C bond construction. The application of the oxidative photoredox strategy to couple C–H bonds next to an oxygen atom with other C–H bonds is more challenging because of the more positive oxidation potential of ethers than that of amines. Here, we take advantage of organic dye 9-mesityl-10-methylacridinium perchlorate (Acr+-Mes ClO4−) as the photosensitizer and BrCCl3 as the terminal oxidant to achieve the addition of β-keto esters to oxonium species, directly generated from isochromans, leading to the formation of alkylation products in the α-position of an oxygen atom under visible light irradiation.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Reactivity and mechanistic insight into the cross coupling reaction between isochromans and β-keto esters through C–H bond activation under visible light irradiation

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