Discovery and Development of an Aerobic Radical Hydroxyarylation Reaction Using Aryl Halides, Olefins, and O2

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-04-17 DOI:10.1021/acs.orglett.5c00968

Mark C. Maust, Defne Tuncaral, Simon B. Blakey

引用次数: 0

Abstract

Herein, we report the development of a radical hydroxyarylation reaction through the coupling of an aryl radical, an olefin, and O₂. Photoredox activation of a silyl radical halogen atom abstractor enables mild aryl radical generation and reactivity in 5-exo, 6-exo, and dearomative cyclizations to synthesize a variety of hydroxylated semisaturated fused ring systems. Expansion of the substrate scope to include aryl bromide starting materials reveals the crucial role of iodide in the catalytic cycle.

Abstract Image

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

芳基卤化物、烯烃和氧的好氧自由基羟化反应的发现和发展

在这里，我们报道了通过芳基自由基、烯烃和O2的偶联，自由基羟基化反应的发展。硅基自由基卤素原子萃取剂的光氧化还原活化使芳基自由基在5-外显子、6-外显子和脱芳香环化中产生和反应，从而合成各种羟基化半饱和融合环体系。扩大底物范围以包括芳基溴起始材料揭示了碘化物在催化循环中的关键作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

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.