Organic Letters
Organic Letters
5 years ago

Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones

Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones
Fumitoshi Kakiuchi, Takuya Kochi, Yoshio Aso, Yutaka Ie, Kohei Yamada, Kentaro Watanabe, Yusuke Suzuki
A convenient method for the syntheses of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes via the ruthenium-catalyzed chemoselective C–O arylation of 1,4- and 1,5-dimethoxyanthraquinones is described. Dimethoxyanthraquinones reacted selectively with arylboronates at the ortho C–O bonds to give diarylation products. An efficient two-step procedure consisting of a Corey–Chaykofsky reaction and subsequent dehydrative aromatization afforded derivatives of dibenzo[h,rst]pentaphenes and dibenzo[fg,qr]pentacenes. Hole-transporting characteristics were observed for a device with a bottom-contact configuration that was fabricated from one of these polycyclic aromatic hydrocarbons.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01666

DOI: 10.1021/acs.orglett.7b01666

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