TY - JOUR
T1 - Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C-O Arylation of Dimethoxyanthraquinones
AU - Suzuki, Yusuke
AU - Yamada, Kohei
AU - Watanabe, Kentaro
AU - Kochi, Takuya
AU - Ie, Yutaka
AU - Aso, Yoshio
AU - Kakiuchi, Fumitoshi
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI Grant Numbers JP15H05839 in Middle Molecular Strategy, and CREST and ACT-C (Grant Number JPMJCR12Y8) from the Japan Science and Technology Agency (JST) Japan. T.K. is also grateful for support by JSPS KAKENHI Grant Number 16H01040 (Precisely Designed Catalysts with Customized Scaffolding). Dedicated to Professor Teruaki Mukaiyama in celebration of his 90th birthday (Sotsuju).
PY - 2017/7/21
Y1 - 2017/7/21
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.orglett.7b01666
DO - 10.1021/acs.orglett.7b01666
M3 - Article
C2 - 28703598
AN - SCOPUS:85025128931
SN - 1523-7060
VL - 19
SP - 3791
EP - 3794
JO - Organic Letters
JF - Organic Letters
IS - 14
ER -