Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides
- 18 November 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 132 (49), 17402-17404
- https://doi.org/10.1021/ja109120n
Abstract
The enantioselective fluorination of readily available cyclic allylic chlorides with AgF has been accomplished using a Pd(0) catalyst and Trost bisphosphine ligand. The reactions proceed with unprecedented ease of operation for Pd-mediated nucleophilic fluorination, allowing access to highly enantioenriched cyclic allylic fluorides that bear diverse functional groups. Evidence that supports a mechanism in which C−F bond formation occurs by an SN2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.Keywords
This publication has 39 references indexed in Scilit:
- Mechanism of C−F Reductive Elimination from Palladium(IV) FluoridesJournal of the American Chemical Society, 2010
- Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual-Catalyst SystemJournal of the American Chemical Society, 2010
- Palladium-Catalyzed Intermolecular Aminofluorination of StyrenesJournal of the American Chemical Society, 2010
- Palladium-Catalyzed Intramolecular Aminofluorination of Unactivated AlkenesJournal of the American Chemical Society, 2009
- Fluorine & chirality: how to create a nonracemic stereogenic carbon–fluorine centre?Chemical Society Reviews, 2009
- Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl FluoridesScience, 2009
- Versatile Pd(OTf)2·2H2O-Catalyzed ortho-Fluorination Using NMP as a PromoterJournal of the American Chemical Society, 2009
- Palladium‐Mediated Fluorination of Arylboronic AcidsAngewandte Chemie-International Edition, 2008
- Carbon−Fluorine Reductive Elimination from a High-Valent Palladium FluorideJournal of the American Chemical Society, 2008
- Palladium-Catalyzed Fluorination of Carbon−Hydrogen BondsJournal of the American Chemical Society, 2006