title: Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C-H functionalization.
abstract: We report a new synthesis of phenanthridines based on palladium-catalyzed picolinamide-directed sequential C-H functionalization reactions starting from readily available benzylamine and aryl iodide precursors. Under the catalysis of Pd(OAc)2, the ortho-C-H bond of benzylpicolinamides is first arylated with an aryl iodide. The resulting biaryl compound is then subjected to palladium-catalyzed picolinamide-directed intramolecular dehydrogenative C-H amination with PhI(OAc)2 oxidant to form the corresponding cyclized dihydrophenanthridines. The benzylic position of these dihydrophenanthridines could be further oxidized with Cu(OAc)2, removing the picolinamide group and providing phenathridine products. The cyclization and oxidation could be carried out in a single step and afford phenathridines in moderate to good yields.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, United States of America.
authors.forename: Ryan
authors.initials: R
authors.lastname: Pearson
authors.forename: Shuyu
authors.initials: S
authors.lastname: Zhang
authors.forename: Gang
authors.initials: G
authors.lastname: He
authors.forename: Nicola
authors.initials: N
authors.lastname: Edwards
authors.forename: Gong
authors.initials: G
authors.lastname: Chen
keywords: C–H functionalization; palladium; phenanthridine; picolinamide