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Updated: Apr 23, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Catalytic wittig reactions of semi- and nonstabilized ylides enabled by ylide tuning
Emma E Coyle1, Bryan J Doonan, Andrew J Holohan
1National Centre for Sensor Research (NCSR), Dublin City University, Glasnevin, Dublin 9 (Ireland).
Abstract:
The first examples of catalytic Wittig reactions with semistabilized and nonstabilized ylides are reported. These reactions were enabled by utilization of a masked base, sodium tert-butyl carbonate, and/or ylide tuning. The acidity of the ylide-forming proton was tuned by varying the electron density at the phosphorus center in the precatalyst, thus facilitating the use of relatively mild bases. Steric modification of the precatalyst structure resulted in significant enhancement of E selectivity up to >95:5, E/Z.
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