title: Palladium-catalyzed regio- and enantioselective fluorination of acyclic allylic halides.
abstract: This report describes the Pd(0)-catalyzed fluorination of linear allylic chlorides and bromides, yielding branched allylic fluorides in high selectivity. Many of the significant synthetic limitations previously associated with the preparation of these products are overcome by this catalytic method. We also demonstrate that a chiral bisphosphine-ligated palladium catalyst enables highly enantioselective access to a class of branched allylic fluorides that can be readily diversified to valuable fluorinated products.
authors: Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
authors: Matthew H
authors: MH
authors: Katcher
authors: Allen
authors: A
authors: Sha
authors: Abigail G
authors: AG
authors: Doyle
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001965:Bromides / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000138:chemical synthesis / Q000737:chemistry*; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D001965:Bromides; D002712:Chlorides; D010165:Palladium; D005459:Fluorides