Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones
Yusuke Suzuki
1
,
Kohei Yamada
1
,
Kentaro Watanabe
1
,
Takuya Kochi
1
,
Yutaka Ie
2, 3
,
Yoshio Aso
2
,
Fumitoshi Kakiuchi
1, 3
Publication type: Journal Article
Publication date: 2017-07-13
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
28703598
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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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13
Total citations:
13
Citations from 2024:
2
(15.38%)
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Suzuki Y. et al. Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones // Organic Letters. 2017. Vol. 19. No. 14. pp. 3791-3794.
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Suzuki Y., Yamada K., Watanabe K., Kochi T., Ie Y., Aso Y., Kakiuchi F. Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones // Organic Letters. 2017. Vol. 19. No. 14. pp. 3791-3794.
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RIS
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TY - JOUR
DO - 10.1021/acs.orglett.7b01666
UR - https://doi.org/10.1021/acs.orglett.7b01666
TI - Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones
T2 - Organic Letters
AU - Suzuki, Yusuke
AU - Yamada, Kohei
AU - Watanabe, Kentaro
AU - Kochi, Takuya
AU - Ie, Yutaka
AU - Aso, Yoshio
AU - Kakiuchi, Fumitoshi
PY - 2017
DA - 2017/07/13
PB - American Chemical Society (ACS)
SP - 3791-3794
IS - 14
VL - 19
PMID - 28703598
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2017_Suzuki,
author = {Yusuke Suzuki and Kohei Yamada and Kentaro Watanabe and Takuya Kochi and Yutaka Ie and Yoshio Aso and Fumitoshi Kakiuchi},
title = {Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones},
journal = {Organic Letters},
year = {2017},
volume = {19},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/acs.orglett.7b01666},
number = {14},
pages = {3791--3794},
doi = {10.1021/acs.orglett.7b01666}
}
Cite this
MLA
Copy
Suzuki, Yusuke, et al. “Synthesis of Dibenzo[h,rst]pentaphenes and Dibenzo[fg,qr]pentacenes by the Chemoselective C–O Arylation of Dimethoxyanthraquinones.” Organic Letters, vol. 19, no. 14, Jul. 2017, pp. 3791-3794. https://doi.org/10.1021/acs.orglett.7b01666.