Ring-Retentive SN2′-Type Alkylation of gem-Dichlorocyclobutenones Enabled by an In Situ Alkene-to-Radical Relay

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-07-31 Epub Date: 2026-07-21 DOI:10.1021/acs.orglett.6c02820

Zexu Su, Jianguo Han, Huifeng Yue

引用次数: 0

Abstract

A photocatalyst-free radical S_N2′-type alkylation of gem-dichlorocyclobutenones with unactivated alkenes is enabled by visible-light-induced C–Zr bond homolysis. Alkylzirconium intermediates generated in situ from terminal or internal alkenes serve as alkyl radical precursors and undergo radical addition/β-fragmentation with gem-dichlorocyclobutenones to afford ring-retained α-chlorocyclobutenones. This protocol avoids preformed radical donors and external photocatalysts, proceeds under mild conditions, tolerates structurally complex substrates, and furnishes multifunctional α-chlorocyclobutenones suitable for further diversification.

查看原文本刊更多论文

原位烯烃-自由基接力实现宝石-二氯环丁烯酮的SN2′型环保持烷基化。

通过可见光诱导的C-Zr键均解，实现了宝石-二氯环丁烯酮与未活化烯烃的光催化自由基SN2′型烷基化反应。末端或内烯烃原位生成的烷基锆中间体作为烷基自由基前体，与宝石-二氯环丁烯酮发生自由基加成/β裂解，生成环保留α-氯环丁烯酮。该工艺避免了预先形成的自由基供体和外部光催化剂，在温和的条件下进行，耐受结构复杂的底物，并提供适合进一步多样化的多功能α-氯环丁烯酮。

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分钟内获得全文求助全文

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.