A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation

Sachin S. Ichake, Bharath Kumar Villuri, Sabbasani Rajasekhara Reddy, Veerababurao Kavala, Ching Fa Yao

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Abstract

The palladium catalyzed synthesis of 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives as core polycyclic aromatic hydrocarbons (PAHs) was achieved via an intramolecular annulation and decyanogenative C-H bond alkenylation strategy. A readily synthesized Knoevenagel condensation product of [1,1′-biphenyl]-2,2′-dicarbaldehyde with benzyl cyanide converted successfully into 14-phenylbenzo[f]tetraphene-9-carbonitrile derivatives in excellent yields up to 94%. The transformation involves an intramolecular cascade C-C bond formation along with a C-H bond cleavage sequence.

Original languageEnglish
Pages (from-to)2256-2260
Number of pages5
JournalOrganic Letters
Volume21
Issue number7
DOIs
Publication statusPublished - 2019 Jan 1

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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