title: Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines.
abstract: A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ε-C(sp(2))-H bonds of γ-arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of γ-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our previously reported PA-directed electrophilic aromatic substitution approach to this transformation. As demonstrated herein, a three step sequence of Pd-catalyzed γ-C(sp(3))-H arylation, Pd-catalyzed ε-C(sp(2))-H iodination, and Cu-catalyzed C-N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns.
authors: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors: William A
authors: WA
authors: Nack
authors: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
authors: Xinmou
authors: X
authors: Wang
authors: Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.
authors: Bo
authors: B
authors: Wang
authors: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States.
authors: Gang
authors: G
authors: He
authors: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States; State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China.
authors: Gong
authors: G
authors: Chen
keywords: iodination; palladium; remote C–H activation; tetrahydroquinoline