可见光诱导苯基的好氧正选择性C-H羟基化反应

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-20 DOI:10.1021/acs.joc.5c00681

Jiaoyue Lv, Huiying Zeng

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引用次数: 0

摘要

在此，我们报道了一个可见光诱导的苯的正选择性C-H羟基化反应，该反应具有良好的官能团耐受性和优异的区域选择性。通过克级实验证明，该方法具有可扩展性，并可进一步应用于类鱼素的合成。对照实验揭示了单线态氧参与反应机理。此外，它通过一个五元环自由基中间体进行，二甲亚砜同时作为溶剂和还原剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Visible-Light-Induced Aerobic ortho-Selective C–H Hydroxylation of Benzils

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Visible-Light-Induced Aerobic ortho-Selective C–H Hydroxylation of Benzils

Herein, we report a visible-light-induced ortho-selective C–H hydroxylation of benzils, which exhibits good functional group tolerance and excellent regioselectivity. This method is scalable, as demonstrated by gram-scale experiments, and is further applied in the synthesis of rotenoids. Control experiments reveal the involvement of singlet oxygen in the reaction mechanism. Moreover, it proceeds via a five-membered ring radical intermediate, with dimethyl sulfoxide serving both as the solvent and reducing agent.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.