由 MeOH 触发的未活化烷基溴的卤素原子转移促成光氧化吉斯加成法

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-18 DOI:10.1021/acs.orglett.5c00923

Xian-Chen He, Yan-Ling Liu, Jie Gao, Ke-Rong Li, Kai Chen, Hao-Yue Xiang, Hua Yang

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引用次数: 0

摘要

在此，我们在温和的条件下，以易于获得的原料 MeOH 作为卤素原子转移 (XAT) 试剂，成功地与易于获得的烷基溴进行了镍催化、光氧化 Giese 加成反应。通过一系列结构各异的烷基溴和吉斯型受体，证明了这一方案的多功能性，并获得了中等至良好的产率。机理研究表明，通过烷基溴的 XAT 形成烷基自由基的过程初步是由 -CH2OH 促成的，而 -CH2OH 是由 MeOH 的顺序光氧化/1,2-氢原子转移而来的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

MeOH-Triggered Halogen-Atom Transfer of Unactivated Alkyl Bromides Enabling the Photoredox Giese Addition

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MeOH-Triggered Halogen-Atom Transfer of Unactivated Alkyl Bromides Enabling the Photoredox Giese Addition

Herein, a nickel-catalyzed, photoredox Giese addition reaction with readily accessible alkyl bromides, driven by readily available feedstock MeOH as the halogen-atom transfer (XAT) reagent, was successfully achieved under mild conditions. The versatility of this protocol was demonstrated through a range of structurally varied alkyl bromides and Giese-type acceptors with moderate to good yields. Mechanistic investigation highlights that the formation of alkyl radicals through the XAT of alkyl bromides was tentatively prompted by ^•CH₂OH, which was derived from the sequential photo-oxidation/1,2-hydrogen-atom transfer of MeOH.

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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.