title: Catalytic wittig reactions of semi- and nonstabilized ylides enabled by ylide tuning.
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.
authors.affiliation: National Centre for Sensor Research (NCSR), Dublin City University, Glasnevin, Dublin 9 (Ireland).
authors.forename: Emma E
authors.initials: EE
authors.lastname: Coyle
authors.forename: Bryan J
authors.initials: BJ
authors.lastname: Doonan
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Holohan
authors.forename: Killian A
authors.initials: KA
authors.lastname: Walsh
authors.forename: Florie
authors.initials: F
authors.lastname: Lavigne
authors.forename: Elizabeth H
authors.initials: EH
authors.lastname: Krenske
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: O'Brien
keywords: Wittig reaction; homogeneous catalysis; olefination; phosphorus; ylide