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

Masayuki Iwasaki, Yasuhiro Araki, Shohei Iino, Yasushi Nishihara

Research output: Contribution to journalArticle

36 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9247-9263
Number of pages17
JournalJournal of Organic Chemistry
Volume80
Issue number18
DOIs
Publication statusPublished - Sep 18 2015

ASJC Scopus subject areas

  • Organic Chemistry

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