Short synthesis of alkyl-substituted acenes using carbonyl-directed C-H and C-O functionalization

Daiki Matsumura, Kentaroh Kitazawa, Seiya Terai, Takuya Kochi, Yutaka Ie, Masashi Nitani, Yoshio Aso, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A convenient method for the synthesis of tetraalkylanthracenes and -pentacenes by means of ruthenium-catalyzed regioselective C-H alkylation of the corresponding acenequinones was developed. Dialkyldiarylpentacene was also synthesized using chemoselective tandem C-H alkylation/C-O arylation of dimethoxypentacenequinone. It was suggested that a tetraalkylpentacene is stable under air in the dark and possesses an appropriate HOMO level as active material for p-type organic field-effect transistors (OFETs).

Original languageEnglish
Pages (from-to)3882-3885
Number of pages4
JournalOrganic Letters
Volume14
Issue number15
DOIs
Publication statusPublished - 2012 Aug 3

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alkylation
Alkylation
Organic field effect transistors
Ruthenium
synthesis
ruthenium
field effect transistors
Air
air

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Short synthesis of alkyl-substituted acenes using carbonyl-directed C-H and C-O functionalization. / Matsumura, Daiki; Kitazawa, Kentaroh; Terai, Seiya; Kochi, Takuya; Ie, Yutaka; Nitani, Masashi; Aso, Yoshio; Kakiuchi, Fumitoshi.

In: Organic Letters, Vol. 14, No. 15, 03.08.2012, p. 3882-3885.

Research output: Contribution to journalArticle

Matsumura, Daiki ; Kitazawa, Kentaroh ; Terai, Seiya ; Kochi, Takuya ; Ie, Yutaka ; Nitani, Masashi ; Aso, Yoshio ; Kakiuchi, Fumitoshi. / Short synthesis of alkyl-substituted acenes using carbonyl-directed C-H and C-O functionalization. In: Organic Letters. 2012 ; Vol. 14, No. 15. pp. 3882-3885.
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AU - Aso, Yoshio

AU - Kakiuchi, Fumitoshi

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