Palladium-Catalyzed Reaction of Haloarenes with Diarylethynes: Synthesis, Structural Analysis, and Properties of Methylene-Bridged Arenes

Che Wei Lee, En Chih Liu, Yao Ting Wu

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Fluorenes and methylene-bridged polyarenes were easily and efficiently synthesized from haloarenes (or aryl triflates) and diarylethynes by a one-pot, two-step procedure. This protocol involves the palladium-catalyzed cycloisomerization and a subsequent base-mediated retro-aldol condensation. A major advantage is that the starting materials need not have ortho functional groups to complete the annulation. The backbone of the designed products was enlarged using dihaloarenes, highly π-conjugated haloarenes, or diarylalkynes. The mechanism of the formation of benzo[a]fluorene was investigated. The bowl-shaped structure of methylene-bridged indenocorannulene was verified by X-ray crystallography. The photophysical and electrochemical properties of the products thus prepared were investigated.

Original languageEnglish
Pages (from-to)10446-10456
Number of pages11
JournalJournal of Organic Chemistry
Volume80
Issue number21
DOIs
Publication statusPublished - 2015 Nov 6

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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