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Updated: May 27, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Two Distinct Diazo-Diazo Cross-Coupling Reactions between α-Aryldiazo Ketones and Vinyldiazo Esters Using Gold
Debashis Barik1, Rai-Shung Liu2
1Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
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.
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