Visible-Light-Enabled Catalytic Intramolecular Double Oxidation of Olefins to ortho-Hydroxylactones

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-13 DOI:10.1021/acs.orglett.4c03875

Guangxian Chen, Boyi Liu, Lele Zhang, Feiwei Yan, Sanmei Pan, Feiming Li, Zhixiong Cai, Xiaoping Chen, Shunyou Cai

引用次数: 0

Abstract

We have effectively utilized cost-effective 2-bromoanthraquinone as a photocatalyst to develop an efficient and environmentally friendly method for producing o-hydroxy lactones under mild visible light irradiation. Importantly, this protocol only relies on oxygen as an oxidant, completely eliminating the need for additional chemical reagents and showcasing a sustainable approach to chemical transformation. Operating at room temperature, we utilized a mixed solvent system of DMF and CHCl₃, which greatly facilitated the selective conversion of various 2-vinylbenzoic acids and carboxylic acids to functional o-hydroxyl lactones. The process also exhibited excellent diastereoselectivity. Moreover, this versatile strategy is compatible with a wide range of biologically active and complex molecules, offering new opportunities for late-stage structural modifications of these compounds.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.