Convenient synthesis of Dibenzo[a, h]anthracenes and picenes via C-H arylation of acetophenones with arenediboronates

Kentaroh Kitazawa; Takuya Kochi; Masashi Nitani; Yutaka Ie; Yoshio Aso; Fumitoshi Kakiuchi

doi:10.1246/cl.2011.300

Convenient synthesis of Dibenzo[a, h]anthracenes and picenes via C-H arylation of acetophenones with arenediboronates

Kentaroh Kitazawa, Takuya Kochi, Masashi Nitani, Yutaka Ie, Yoshio Aso, Fumitoshi Kakiuchi

Department of Chemistry

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

36 Citations (Scopus)

Abstract

A new convenient method for the synthesis of dibenzo-[a, h]anthracenes and picenes using ruthenium-catalyzed regioselective C-H arylation of aromatic ketones has been developed. Acetophenone derivatives and 1, 4-benzenediboronates were coupled in 2:1 ratios to form p-terphenyl derivatives. Conversion of the acetyl group to an ethynyl group, followed by cycloaromatization provided the desired fused aromatic compounds. An organic field-effect transistor fabricated from one of these products gave moderate hole mobility.

Original language	English
Pages (from-to)	300-302
Number of pages	3
Journal	Chemistry Letters
Volume	40
Issue number	3
DOIs	https://doi.org/10.1246/cl.2011.300
Publication status	Published - 2011

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.2011.300

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abstract = "A new convenient method for the synthesis of dibenzo-[a, h]anthracenes and picenes using ruthenium-catalyzed regioselective C-H arylation of aromatic ketones has been developed. Acetophenone derivatives and 1, 4-benzenediboronates were coupled in 2:1 ratios to form p-terphenyl derivatives. Conversion of the acetyl group to an ethynyl group, followed by cycloaromatization provided the desired fused aromatic compounds. An organic field-effect transistor fabricated from one of these products gave moderate hole mobility.",

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AU - Nitani, Masashi

AU - Ie, Yutaka

AU - Aso, Yoshio

AU - Kakiuchi, Fumitoshi

PY - 2011

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AB - A new convenient method for the synthesis of dibenzo-[a, h]anthracenes and picenes using ruthenium-catalyzed regioselective C-H arylation of aromatic ketones has been developed. Acetophenone derivatives and 1, 4-benzenediboronates were coupled in 2:1 ratios to form p-terphenyl derivatives. Conversion of the acetyl group to an ethynyl group, followed by cycloaromatization provided the desired fused aromatic compounds. An organic field-effect transistor fabricated from one of these products gave moderate hole mobility.

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Convenient synthesis of Dibenzo[a, h]anthracenes and picenes via C-H arylation of acetophenones with arenediboronates

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