Gold-Catalyzed Regiospecific C−H Annulation of o-Ethynylbiaryls with Anthranils: π-Extension by Ring-Expansion En Route to N-Doped PAHs

Zhongyi Zeng, Hongming Jin, Kohei Sekine, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed π-extension of anthranils with o-ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and shows good functional-group compatibility as well as scale-up potential. Mechanistically, the tandem reaction is proposed to involve a nucleophilic addition/ring opening/regiospecific C−H annulation/protodeauration sequence terminated by a Friedel–Crafts-type cyclization. Photophysical studies of the products indicated violet-blue fluorescence emission with quantum yields up to 0.45.

Original languageEnglish
Pages (from-to)6935-6939
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number23
DOIs
Publication statusPublished - Jun 4 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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