Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-05 DOI:10.1021/acs.orglett.5c00631
Yu Hong, Jun Xu, An Chen, Yating Du, Guangze Wang, Jiabin Shen, Pengfei Zhang
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Abstract

Herein, we introduce an efficient and straightforward strategy for the selective C–H esterification and alkylation of quinoxalin-2(1H)-ones with aldehydes. A key feature of our study is the ability to perform both C–H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1H)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields. The applicability of this approach is further enhanced by its scalability through continuous-flow synthesis, late-stage modification of significant molecules, and product derivatization. Our mechanistic investigations reveal a radical relay mechanism, triggered by a hydrogen atom transfer process.

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可见光诱导喹啉-2(1H)- 1与醛类在温和条件下的发散碳氢酯化/烷基化反应
本文介绍了喹啉-2(1H)- 1与醛选择性C-H酯化和烷基化的一种有效而直接的策略。我们研究的一个关键特征是使用不同类型的醛进行C-H酯化和烷基化的能力。该反应体系与一系列喹诺沙林-2(1H)-酮和醛具有很高的相容性,以中高收率生产c3 -酯化和c3 -烷基化产物。通过连续流合成、重要分子的后期修饰和产品衍生化,该方法的适用性进一步增强。我们的机理研究揭示了一个由氢原子转移过程触发的自由基接力机制。
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来源期刊
Organic Letters
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.
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