title: Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis.
abstract: Herein we report a highly meta-selective C-H arylation using simple tertiary amines as the directing group. This method takes advantage of Pd/norbornene catalysis, offering a distinct strategy to control the site selectivity. The reaction was promoted by commercially available AsPh3 as the ligand and a unique "acetate cocktail". Aryl iodides with an ortho electron-withdrawing group were employed as the coupling partner. A wide range of functional groups, including some heteroarenes, are tolerated under the reaction conditions. In addition, the amine directing group can be easily installed and transformed to other common versatile functional groups. We expect this C-H functionalization mode to have broad implications for developing other meta-selective transformations beyond this work.
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Dong
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
authors.forename: Jianchun
authors.initials: J
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.
authors.forename: Guangbin
authors.initials: G
authors.lastname: Dong
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000588:Amines; D006841:Hydrocarbons, Aromatic; D009636:Norbornanes; D009942:Organometallic Compounds; D010165:Palladium