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 journalArticle

31 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

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Cyclization
Polycyclic Aromatic Hydrocarbons
Quantum yield
Polycyclic aromatic hydrocarbons
Gold
Functional groups
Fluorescence
Atoms

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Gold-Catalyzed Regiospecific C−H Annulation of o-Ethynylbiaryls with Anthranils : π-Extension by Ring-Expansion En Route to N-Doped PAHs. / Zeng, Zhongyi; Jin, Hongming; Sekine, Kohei; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.

In: Angewandte Chemie - International Edition, Vol. 57, No. 23, 04.06.2018, p. 6935-6939.

Research output: Contribution to journalArticle

Zeng, Zhongyi ; Jin, Hongming ; Sekine, Kohei ; Rudolph, Matthias ; Rominger, Frank ; Hashmi, A. Stephen K. / Gold-Catalyzed Regiospecific C−H Annulation of o-Ethynylbiaryls with Anthranils : π-Extension by Ring-Expansion En Route to N-Doped PAHs. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 23. pp. 6935-6939.
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