Visible‐Light‐Mediated Regioselective Trichloromethyl Hydroxylation of Alkenes: A Metal‐Free Strategy for β‐Trichloromethyl Alcohols

IF 2.7 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-10-01 DOI:10.1002/ajoc.202500511

Xian Jiang , Duoduo Xiao , Renhua Su , Yanfu Jiang , Jiantao Zhang , Weibing Liu , Peng Zhou

引用次数: 0

Abstract

A visible light‐driven, metal‐free strategy for the regioselective synthesis of β‐trichloromethyl alcohols has been developed through a three‐component reaction of alkenes with CCl₄ and TBHP under mild blue LED irradiation. This method achieves vicinal trichloromethyl hydroxylation with broad substrate scope and good functional group tolerance. Mechanistic studies revealed a radical pathway in which TBHP acts as the hydroxyl donor. The protocol operates under ambient conditions without transition metals, offering a sustainable and scalable platform for synthesizing polyhalogenated building blocks with potential applications in medicinal chemistry and synthetic transformations.

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可见光介导的区域选择性三氯甲基烯烃羟基化：β-三氯甲基醇的无金属策略

在温和的蓝色LED照射下，通过烯烃与CCl4和TBHP的三组分反应，开发了一种可见光驱动，无金属的区域选择性合成β-三氯甲基醇的策略。该方法具有底物范围广、官能团耐受性好等优点。机制研究揭示了thbhp作为羟基供体的自由基途径。该方案在无过渡金属的环境条件下运行，为合成多卤化构建块提供了一个可持续和可扩展的平台，在药物化学和合成转化中具有潜在的应用。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.