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Updated: Oct 14, 2025

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
Published on: January 30, 2015
A Chan-Evans-Lam approach to trisubstituted vinyl ethers
Jonathan K Sader1, Bryce A Molder1, Jeremy E Wulff1
1Department of Chemistry, University of Victoria, PO Box 3065 STN CSC, Victoria, British Columbia, Canada, V8W 3V6. wulff@uvic.ca.
Chan-Evans-Lam coupling of vinyl trifluoroborates and alcohols provides a new route to trisubstituted vinyl ethers. This method offers an alternative to prior techniques and enables further synthesis of valuable organic compounds.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
- Catalysis
Background:
- Trisubstituted vinyl ethers are important synthetic intermediates.
- Previous methods for their synthesis had limitations, such as requiring neat liquid alcohol coupling partners.
Purpose of the Study:
- To develop a new and improved method for accessing trisubstituted vinyl ethers.
- To explore the utility of the synthesized vinyl ethers in further chemical transformations.
Main Methods:
- Chan-Evans-Lam coupling reaction between vinyl trifluoroborates and primary aliphatic alcohols.
- Palladium-catalyzed redox-relay Heck reaction for subsequent functionalization.
Main Results:
- Successful synthesis of trisubstituted vinyl ethers using the Chan-Evans-Lam coupling.
- Demonstrated that the developed method does not require neat liquid alcohol coupling partners.
- Conversion of vinyl ethers into aldehyde-functionalized 1,3-dihydroisobenzofurans via Heck reaction.
Conclusions:
- The Chan-Evans-Lam coupling offers a valuable alternative for synthesizing trisubstituted vinyl ethers.
- The developed methodology expands synthetic possibilities for accessing complex organic molecules.
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