title: Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp(3))-H Bonds.
abstract: The transition-metal-catalyzed direct C-H bond fluorination is an attractive synthetic tool toward the preparation of organofluorines. While many methods exist for the direct sp(3) C-H functionalization, site-selective fluorination of unactivated sp(3) carbons remains a challenge. Direct, highly site-selective and diastereoselective fluorination of aliphatic amides via a palladium-catalyzed bidentate ligand-directed C-H bond functionalization process on unactivated sp(3) carbons is reported. With this approach, a wide variety of β-fluorinated amino acid derivatives and aliphatic amides, important motifs in medicinal and agricultural chemistry, were prepared with palladium acetate as the catalyst and Selectfluor as the fluorine source.
authors.affiliation: †Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, United States.
authors.forename: Jinmin
authors.initials: J
authors.lastname: Miao
authors.forename: Ke
authors.initials: K
authors.lastname: Yang
authors.affiliation: †Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, United States.
authors.forename: Martin
authors.initials: M
authors.lastname: Kurek
authors.affiliation: †Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, Indianapolis, Indiana 46202, United States.
authors.forename: Haibo
authors.initials: H
authors.lastname: Ge
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D006845:Hydrocarbons, Fluorinated; D005461:Fluorine; D010165:Palladium