Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 18, Pages 9247-9263Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01693
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Funding
- JSPS [26810060]
- Foundation for Interaction in Science & Technology, Japan
- Grants-in-Aid for Scientific Research [26810060] Funding Source: KAKEN
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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)-,beta-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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