title: Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines.
abstract: A Rh(III)-catalyzed C-H functionalization approach was developed for the preparation of multisubstituted 3-fluoropyridines from α-fluoro-α,β-unsaturated oximes and alkynes. Oximes substituted with aryl, heteroaryl, and alkyl β-substituents were effective coupling partners, as were symmetrical and unsymmetrical alkynes with aryl and alkyl substituents. The first examples of coupling α,β-unsaturated oximes with terminal alkynes was also demonstrated and proceeded with uniformly high regioselectivity to provide single 3-fluoropyridine regioisomers. Reactions were also conveniently set up in air on the benchtop.
authors.affiliation: †Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
authors.forename: Shuming
authors.initials: S
authors.lastname: Chen
authors.affiliation: ‡Division of Chemical Sciences, Lawrence Berkeley National Laboratory, and Department of Chemistry, University of California-Berkeley, Berkeley, California 94720, United States.
authors.forename: Robert G
authors.initials: RG
authors.lastname: Bergman
authors.affiliation: †Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D002384:Catalysis; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D006845:Hydrocarbons, Fluorinated; D016566:Organoselenium Compounds; D011725:Pyridines; D012238:Rhodium