Related Experiment Video
Updated: Aug 26, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Pd-Promoted Cyclization of (Z)-Pent-2-en-4-yn-1-yl Alkanoates Leading to Furans via an Acyl Group Shift and Further
Ai-Chun Chiang1, Yi-Hung Liu1, Shie-Ming Peng1
1Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan.
Abstract:
Palladium-promoted acyl migration was observed in the reaction of (Z)-pent-2-en-4-yn-1-yl alkanoates in the presence of DBU to yield 2-(alkanoylmethyl)furan derivatives (2) in high yields. Compounds 2 then underwent oxidative decarbonylation to afford 2-acylfurans with O2 as the oxidant under mild and metal-free conditions. The mechanistic pathway of the reaction involving an intramolecular cyclization and acyl group shift is discussed.
Related Concept Videos
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis

