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

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 Epub Date: 2025-02-19 DOI:10.1021/acs.orglett.5c00068

Debashis Barik, Rai-Shung Liu

引用次数: 0

Abstract

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.

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

求助全文

约1分钟内获得全文去求助

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.