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

doi:10.1021/ol301608m

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

29 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 language	English
Pages (from-to)	3882-3885
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	15
DOIs	https://doi.org/10.1021/ol301608m
Publication status	Published - 2012 Aug 3

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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).",

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T1 - Short synthesis of alkyl-substituted acenes using carbonyl-directed C-H and C-O functionalization

AU - Matsumura, Daiki

AU - Kitazawa, Kentaroh

AU - Terai, Seiya

AU - Kochi, Takuya

AU - Ie, Yutaka

AU - Nitani, Masashi

AU - Aso, Yoshio

AU - Kakiuchi, Fumitoshi

PY - 2012/8/3

Y1 - 2012/8/3

N2 - 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).

AB - 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).

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

Abstract

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