One-Pot Synthesis of Substituted Benzo[b]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium - Dihydroxyterphenylphosphine Catalyst

被引：37

作者：

Yamaguchi, Miyuki ^{[1
]}

Akiyama, Tomoyo ^{[1
]}

Sasou, Hirohisa ^{[1
]}

Katsumata, Haruka ^{[1
]}

Manabe, Kei ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, 52-1 Yada, Shizuoka 4228526, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 13期

关键词：

C-H ACTIVATION; OLIGOARENE-TYPE PHOSPHINES; 4-SUBSTITUTED INDOLES; GRIGNARD-REAGENTS; INTRAMOLECULAR HYDROAMINATION; COMBINATORIAL SYNTHESIS; 2-SUBSTITUTED INDOLES; SONOGASHIRA REACTION; EFFICIENT SYNTHESIS; COUPLING REACTIONS;

D O I：

10.1021/acs.joc.6b00824

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Disubstituted benzo[b]furans were synthesized by ortho-selective Sonogashira coupling of dichlorophenols and terminal alkynes, followed by cyclization and Suzuki-Miyaura coupling in one pot, using a palladium-dihydroxyterphenylphosphine (Cy-DHTP) catalyst. The use of substoichiometric amounts of tetrabutylammonium chloride was effective in accelerating the Suzuki-Miyaura coupling. This protocol was also successfully applied to the one-pot synthesis of disubstituted indoles from dichloroaniline derivatives.

引用

页码：5450 / 5463

页数：14

共 50 条

[41] Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls
Liang, Zuijun
Zhao, Jinlong
Zhang, Yuhong
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01): : 170 - 177
[42] Palladium-catalyzed one-pot synthesis of polysubstituted furans from alkynoates and 2-yn-1-ols
Huang, Huawen
Jiang, Huanfeng
Cao, Hua
Zhao, Jinwu
Shi, Dabin
TETRAHEDRON, 2012, 68 (14) : 3135 - 3144
[43] Convenient one-pot method for the preparation of polysubstituted benzo[b]- and naphtho[1,2-b]-furans and -thiophenes
Katritzky, AR
Serdyuk, L
Xie, LH
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (06): : 1059 - 1064
[44] One-pot multicomponent domino synthesis of highly functionalized dibenzo[b,d]furans
Jaggavarapu, Satyanaraya Reddy
Bhukta, Swadhapriya
Chatterjee, Rana
Anna, Venkateswara Rao
Dandela, Rambabu
TETRAHEDRON LETTERS, 2023, 123
[45] Catalyst-Free One-Pot Synthesis of 4-Substituted Quinazolines
Li, Lingjie
Zhang, Jing
Tang, Yu
Xu, Kiatian
Zhang, Yuanming
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (10) : 2711 - 2716
[46] One-Pot Synthesis of Substituted Furans Using Cu(OTf)2-Catalyzed Propargylation/Cycloisomerization Tandem Reaction
Pan, Ying-ming
Zhao, Su-yan
Ji, Wen-hua
Zhan, Zhuang-ping
JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (01): : 103 - 109
[47] One-pot Synthesis of Benzamidonaphtho[2,1-b]furans and Benzamidobenzo[b]furans as Novel Polycyclic Heteroaromatic Compounds
Vahabinia, Hamid Reza
Karami, Bahador
Khodabakhshi, Saeed
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2013, 60 (11) : 1323 - 1327
[48] One-pot synthesis of benzo[b]furan and indole inhibitors of tubulin polymerization
Flynn, BL
Hamel, E
Jung, MK
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (12) : 2670 - 2673
[49] Microwave-assisted one-pot nitrene insertion-decarboxylation synthesis of substituted indoles
Miner, Elise
Jones, Graham
Ranasinghe, Nadeesha
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[50] One-pot sequential multi-component reaction: Synthesis of 3-substituted indoles
Borpatra, Paran J.
Deka, Bhaskar
Rajbongshi, Basanta K.
Deb, Mohit L.
Baruah, Pranjal K.
SYNTHETIC COMMUNICATIONS, 2018, 48 (16) : 2074 - 2082

← 1 2 3 4 5 →