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

化学科

研究成果: Article › 査読

28 被引用数 (Scopus)

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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).

本文言語	English
ページ（範囲）	3882-3885
ページ数	4
ジャーナル	Organic Letters
巻	14
号	15
DOI	https://doi.org/10.1021/ol301608m
出版ステータス	Published - 2012 8月 3

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol301608m

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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

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