Reductive N-Heterocyclic Carbene Catalysis via Hydride Transfer: Generating Homoenolates from Unsaturated Esters.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-27 DOI:10.1021/acs.orglett.5c01604

Mingyi Pan,Qingyun Wang,Pengcheng Zheng,Yonggui Robin Chi

引用次数: 0

Abstract

In N-heterocyclic carbene (NHC) catalysis, the reduction of NHC-bound acyl azolium species is achieved with progress limited to the generation of ketyl radical intermediates. Here, we report a novel NHC-catalyzed reductive mode for acyl azolium intermediates, which accept a hydride to generate the Breslow intermediate. Then, the reaction of the Breslow intermediate with chalcone results in the formation of cyclopentene, demonstrating a classic umpolung transformation. We expect that this catalytic reductive mode will open new avenues for synthetic transformations.

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通过氢化物转移还原n -杂环羰基催化：由不饱和酯生成同烯醇酯。

在n -杂环碳（NHC）催化中，NHC结合的酰基唑类物质的还原是实现的，但进展仅限于生成酮基自由基中间体。在这里，我们报道了一种新的nhc催化的酰唑中间体的还原模式，该模式接受氢化物生成Breslow中间体。然后，Breslow中间体与查尔酮反应生成环戊烯，证明了一个经典的umpolung转化。我们期望这种催化还原模式将为合成转化开辟新的途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.