双光氧化还原和铬催化1,3-二烯与醛和环丙醇二烷基化制同丙烯醇

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-27 DOI:10.1021/acs.orglett.5c00975

Gaochen Xu, Pei Guan, Longyu Deng, Caipeng Wang, Delong Ma, Yan Meng, Zheng Fang, Jindian Duan, Kai Guo

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引用次数: 0

摘要

本文描述了使用双光氧化还原和铬催化的可见光诱导的醛、1,3-二烯和环丙醇的三组分偶联。该方案实现了1,3-二烯向1,4-二取代均丙烯醇的二烷基化反应，产率中至高，具有良好的区域选择性，反应条件温和，官能团耐受性好，可实现克级合成。机理研究表明，光诱导环丙醇序开环、自由基和亲核级联加成参与了催化循环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Dialkylation of 1,3-Dienes with Aldehydes and Cyclopropanols toward Homoallylic Alcohols by Dual Photoredox and Chromium Catalysis

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Dialkylation of 1,3-Dienes with Aldehydes and Cyclopropanols toward Homoallylic Alcohols by Dual Photoredox and Chromium Catalysis

A visible-light-induced three-component coupling of aldehydes, 1,3-dienes, and cyclopropyl alcohols using dual photoredox and chromium catalysis is herein described. This efficient protocol achieves the dialkylation of 1,3-dienes toward 1,4-disubstituted homoallylic alcohols in moderate to good yields with excellent regioselectivity, featuring mild reaction conditions, good functional group tolerance, and gram-scale synthesis. Mechanistic study suggests that photoinduced sequential ring opening of cyclopropyl alcohol and radical and nucleophilic cascade addition are involved in the catalytic cycle.

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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.