金催化剂和四丁基氟化铵催化α-芳基重氮酮与乙烯基重氮酯的两种不同重氮-重氮交叉偶联反应

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-19 DOI:10.1021/acs.orglett.5c0006810.1021/acs.orglett.5c00068

Debashis Barik, and , Rai-Shung Liu*,

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引用次数: 0

摘要

研究了α-芳基重氮酮与乙烯基重氮酯在金催化剂（5摩尔%）和Bu4NF启动子（1.5摩尔%）催化下的两种不同的偶联反应。这一新的合成方案涉及α-芳基重氮酮在热条件下预先重排生成二芳基烯酮，而乙烯基重氮酯作为亲核试剂产生可分离的4-硅氧基-1-重氮-4-烯-2-酮。该重氮-重氮交叉偶联反应采用金催化剂和Bu4NF促进剂制备了高取代环戊烯酮和取代吡唑衍生物。

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Two Distinct Diazo–Diazo Cross-Coupling Reactions between α-Aryldiazo Ketones and Vinyldiazo Esters Using Gold Catalyst and Tetrabutylammonium Fluoride

Two distinct coupling reactions of α-aryldiazo ketones with vinyldiazo esters are described using gold catalyst (5 mol %) and Bu₄NF promoter (1.5 equiv), respectively. This new synthetic scheme involves a prior rearrangement of α-aryldiazo ketones to generate diarylketenes under thermal conditions whereas vinyldiazo esters serve as nucleophiles to afford isolable 4-siloxy-1-diazo-pent-4-en-2-ones. This diazo–diazo cross-coupling reaction yields highly substituted cyclopentenones using gold catalyst and substituted pyrazole derivatives with Bu₄NF promoter.

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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.