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

Research output: Contribution to journalArticle

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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Alkenylation
Polycyclic Aromatic Hydrocarbons
Palladium
cyanides
polycyclic aromatic hydrocarbons
palladium
cleavage
cascades
condensation
Derivatives
synthesis
products
Condensation
triphenylene
benzyl cyanide
diphenyl

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation. / Ichake, Sachin S.; Villuri, Bharath Kumar; Reddy, Sabbasani Rajasekhara; Kavala, Veerababurao; Yao, Ching Fa.

In: Organic Letters, Vol. 21, No. 7, 01.01.2019, p. 2256-2260.

Research output: Contribution to journalArticle

Ichake, Sachin S. ; Villuri, Bharath Kumar ; Reddy, Sabbasani Rajasekhara ; Kavala, Veerababurao ; Yao, Ching Fa. / A Synthetic Strategy for the Construction of Functionalized Triphenylene Frameworks via Palladium Catalyzed Intramolecular Annulation/Decyanogenative C-H Bond Alkenylation. In: Organic Letters. 2019 ; Vol. 21, No. 7. pp. 2256-2260.
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