title: Palladium-catalyzed asymmetric synthesis of allylic fluorides.
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 S(N)2-type attack of fluoride on a Pd(II)-allyl intermediate is presented.
authors.affiliation: Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Matthew H
authors.initials: MH
authors.lastname: Katcher
authors.forename: Abigail G
authors.initials: AG
authors.lastname: Doyle
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D010165:Palladium; D005459:Fluorides