Alkaline Aqueous Solution Promoted Debromination of 1,2 Dibromo-Fluorocarbons – a Convenient Method for Electron Deficient Perfluorovinyl Ethers
Document Type
Article
Publication Date
1-1-2017
Description
A facile and efficient base-mediated protocol for debromination of vic-dibromides in perfluoroalkyl(aryl) compounds in aqueous medium has been demonstrated. With mild reaction conditions, the developed strategy has a good substrate scope and electron-deficient olefin products were obtained in good yields. A mechanistic explanation of the debromination is offered with three key experimental observations: (1) the reactions are accelerated by the more electron-rich nucleophiles, (2) the reactions are promoted by the more electron poor vic-dibromides in perfluoroalkyl compounds, and (3) the nucleophilic side reaction is preventable. It is evident that the electronic factors strongly dictate vic-dibromides elimination to the perfluorovinyl ethers, which are the precursors for various perfluorinated polymers. The different reaction conditions were tested in implicit solvent (water) conditions, which helped to confirm the E2-like mechanism.
Citation Information
Mei, Hua; McCloud, Rebecca; Ibrahim, Faisal; Nworie, Chimaroke; and Musket, Anna. 2017. Alkaline Aqueous Solution Promoted Debromination of 1,2 Dibromo-Fluorocarbons – a Convenient Method for Electron Deficient Perfluorovinyl Ethers. Tetrahedron Letters. Vol.58(21). 2026-2030. https://doi.org/10.1016/j.tetlet.2017.04.025 ISSN: 0040-4039