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

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.

SUBMITTER: Barik D 

PROVIDER: S-EPMC11877532 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature