Synthesis of Fluorescent 4-Azapyrenes by Palladium(II)-Catalyzed Dual C−H Bond Activation and Annulation

Huan Chang Hsiao, Pratheepkumar Annamalai, Jayachandran Jayakumar, Shang You Sun, Shih Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Unique dual-emissive and deep-blue/green fluorescent multi-substituted 4-azapyrenes with bathochromic shift emission, quantum yields up to 0.60 and long excited-state lifetime were synthesized successfully by annulative π-extension reactions. This synthesis constitutes a palladium-catalyzed dehydrogenative annulation of N-acyl-2-aminobiaryls with in situ 1,3-diynes as a key step, giving substituted phenanthrenes via a rollover C−H bond activation, followed by Bischler-Napieralski cyclization. Further π-extension by superacid-mediated cyclization produced a blue fluorescent naphtho 4-azapyrene. (Figure presented.).

Original languageEnglish
Pages (from-to)1695-1701
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume363
Issue number6
DOIs
StatePublished - Mar 2021

Keywords

  • 4-azapyrene
  • C−H activation
  • fluorescence
  • palladium catalysis
  • phenanthrene

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