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Updated: Dec 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Triarylborane-Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
Ayan Dasgupta1, Katarína Stefkova1, Rasool Babaahmadi2
1Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Cymru/Wales, UK.
Abstract:
Herein we report a facile, mild reaction protocol to form carbon-carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10-20 mol %) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36-87 %). DFT studies were used to elucidate the mechanism for this alkenylation reaction.
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