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

The Journal of Organic Chemistry
Masayuki IwasakiYasushi Nishihara

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.

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Citations

Aug 17, 2018·Chemical Society Reviews·Feijie SongZhang-Jie Shi
May 19, 2020·Angewandte Chemie·Tatsuhiro Tsukamoto, Guangbin Dong
Dec 9, 2020·Organic Letters·Farnaz JafarpourRobert C Ferrier
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Jul 9, 2020·Chemical Reviews·Marius D R Lutz, Bill Morandi
Nov 5, 2021·Organic & Biomolecular Chemistry·Yang LongXiangge Zhou

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