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.
|Original language||English (US)|
|Number of pages||3|
|Journal||Journal of the American Chemical Society|
|State||Published - Dec 15 2010|
ASJC Scopus subject areas
- Colloid and Surface Chemistry