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

Debashis Barik 和 Rai-Shung Liu
Organic letters, 卷.27(8), 頁碼.1871-1877
28/02/2025
PMID: 39970270
Web of Science ID: WOS:001425844600001

摘要

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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https://doi.org/10.1021/acs.orglett.5c00068檢視
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