Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization

被引：1

作者：

Hu Xiaojing ^{[1
]}

Guo Feixiang ^{[1
]}

Zhu Runqing ^{[2
]}

Zhou Bingqi ^{[2
]}

Zhang Tao ^{[2
]}

Fang Lizhen ^{[2
]}

机构：

[1] Xinxiang Med Univ, Affiliated Hosp 3, Xinxiang 453003, Henan, Peoples R China

[2] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 43卷 / 06期

关键词：

transition metal catalysis; regioselectivity hydroxylation; C-H activation; p-alkoxy phenol; HYDROXYLATION;

D O I：

10.6023/cjoc202209012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

p-Alkoxy phenol (p-AOPs) compounds were obtained by one-step selective hydroxylation of alkoxyl-aryl ethers with the transition metal ruthenium(II) as catalyst and [bis(trifluoroacetoxy)iodo]benzene (PIFA) as oxidant. These p-AOPs could be easily converted to quinone monoacetals (QMAs) after dearomatization. Condensation of the QMAs with ss-naphthols provided polycyclic benzofurans which have a wide application prospect. The protocol established in this paper offered a facile and reliable way for the synthesis of these important compounds.

引用

页码：2239 / 2244

页数：6

共 30 条

[1] David J., 1972, [No title captured], Patent No. 2126169
[2] Palladium-Catalyzed Aryl C(sp2)-H Bond Hydroxylation of 2-Arylpyridine Using TBHP as Oxidant
Dong, Jiawei
Liu, Ping
Sun, Peipei
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05): : 2925 - 2929
[3] Synthesis of Chiral Dihydrobenzofurans and Phthalides by Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution: A Strategy for Total Synthesis of Daldinins A, B, and C and Concentricolide
Fang, Lizhen
Lyu, Qinghua
Lu, Chenjuan
Li, Huanhuan
Liu, Saisai
Han, Lili
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (20) : 3196 - 3200
[4] Gu Y. G., 2008, [No title captured], Patent No. 2008079610
[5] Electrochemical Oxidative [4+2] Annulation for the π-Extension of Unfunctionalized Heterobiaryl Compounds
Hu, Xia
Nie, Lei
Zhang, Guoting
Lei, Aiwen
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (35) : 15238 - 15243
[6] Micellar system in copper-catalysed hydroxylation of arylboronic acids: facile access to phenols
Inamoto, Kiyofumi
Nozawa, Kanako
Yonemoto, Misato
Kondo, Yoshinori
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (42) : 11775 - 11777
[7] Metal-Free, Bronsted Acid-Catalyzed Formal [3+2] Annulation of Quinone Monoacetals with 2-Naphthols
Jacob, Anu
Roy, Tony
Kaicharla, Trinadh
Biju, Akkattu T.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20): : 11269 - 11274
[8] Heteroarenes as high performance organic semiconductors
Jiang, Wei
Li, Yan
Wang, Zhaohui
[J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (14) : 6113 - 6127
[9] PALLADIUM CATALYZED TRANSFORMATION OF BENZENE TO PHENOL WITH MOLECULAR-OXYGEN
JINTOKU, T
NISHIMURA, K
TAKAKI, K
FUJIWARA, Y
[J]. CHEMISTRY LETTERS, 1990, (09) : 1687 - 1688
[10] [3+2] Coupling of Quinone Monoacetals with Vinyl Ethers Effected by Tetrabutylammonium Triflate: Regiocontrolled Synthesis of 2-Oxygenated Dihydrobenzofurans
Kamitanaka, Tohru
Tsunoda, Yusuke
Fujita, Yuriko
Dohi, Toshifumi
Kita, Yasuyuki
[J]. ORGANIC LETTERS, 2021, 23 (23) : 9025 - 9029

← 1 2 3 →