Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-26 DOI:10.1021/acs.orglett.4c04494

Shu Wang, Ge Liang, Cheng Wang, Chen-Hong Wang, Zhiyuan Huang, Chen-Ho Tung, Li-Zhu Wu

引用次数: 0

Abstract

Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp³)–H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).

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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.