Fe(III)-Catalyzed Ring Expansion of Cyclopropenone from Olefins via Radicals to Access Pyrone and Indanone Derivatives

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-11 DOI:10.1021/acs.orglett.4c04492

Yao Xiao, Dong-Wei Huang, Jie Liao, Bei Wang, Yu-Long Li, Ji-Yu Wang

引用次数: 0

Abstract

A novel approach for the synthesis of pyrone and indanone derivatives utilizing Fe(III)-catalyzed reductive radical ring expansion of olefins and cyclopropenone has been proposed. The preliminary mechanism study shows that the alkyl radical is formed by hydrogen atom transfer, which can open the tension ring and then generate the intermediate. There are two paths for the intermediate: when there is a hydroxyl group at the β-position of the olefin, the reaction produces pyrones, and otherwise 1-indanone is generated. This method has mild conditions and wide substrate adaptability and allows the indanone fragment to be conveniently accessed.

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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.