title: Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of o-Iodobiphenyls or (Z)-β-Halostyrenes with o-Bromobenzyl Alcohols through Two Sequential C-C Bond Formations Catalyzed by a Palladium Complex.
abstract: o-Bromobenzyl alcohol has been developed as a novel annulating reagent, bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular cyclization. An array of experimental data suggest that the reaction mechanism involves the equilibrium of 1,4-palladium migration.
authors: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors: Masayuki
authors: M
authors: Iwasaki
authors: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors: Yasuhiro
authors: Y
authors: Araki
authors: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
authors: Shohei
authors: S
authors: Iino
authors: Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, Okayama University , 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.|ACT-C, Japan Science and Technology Agency , Kawaguchi 332-0012, Japan.
authors: Yasushi
authors: Y
authors: Nishihara