title: A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.
abstract: A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Aaron C
authors.initials: AC
authors.lastname: Sather
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Hong Geun
authors.initials: HG
authors.lastname: Lee
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Valentina Y
authors.initials: VY
authors.lastname: De La Rosa
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.|Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Peter
authors.initials: P
authors.lastname: Müller
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D005461:Fluorine / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D010165:Palladium / Q000737:chemistry*; D013696:Temperature
chemical_list: D001965:Bromides; D008024:Ligands; D005461:Fluorine; D010165:Palladium