title: Iodination of remote ortho-C-H bonds of arenes via directed S(E)Ar: a streamlined synthesis of tetrahydroquinolines.
abstract: A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp(3))-H arylation, metal-free ε-C(sp(2))-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: William A
authors.initials: WA
authors.lastname: Nack
authors.forename: Gang
authors.initials: G
authors.lastname: He
authors.forename: Shu-Yu
authors.initials: SY
authors.lastname: Zhang
authors.forename: Chengxi
authors.initials: C
authors.lastname: Lu
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000588:Amines; D011804:Quinolines; D010165:Palladium; C542964:1,2,3,4-tetrahydroquinoline