Copper-catalyzed one-pot tandem reactions toward the synthesis of indoles using o-iodoanilines, acyl chlorides, and Wittig reagents

被引：11

作者：

Huang, Bin ^{[1
]}

Hu, Deqing ^{[1
]}

Wang, Jing ^{[1
]}

Wan, Jie-Ping ^{[1
]}

Liu, Yunyun ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 20期

关键词：

Copper catalysis; C-C coupling; Cascade; Indole; One-pot; N BOND FORMATION; MULTISUBSTITUTED INDOLES; DOMINO REACTIONS; CYCLIZATION; ANNULATION; ANILINES; FUNCTIONALIZATION; AMINATION; ROUTE;

D O I：

10.1016/j.tetlet.2015.03.134

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot reactions of acyl chlorides, Wittig reagents, and o-iodoanilines involving a copper-catalyzed C-C coupling have been realized to provide various indoles. The reactions proceed on the basis of the in situ generation of allenes to incorporate o-iodoanilines via tandem Michael addition, C-C coupling, and tautomerization to afford indoles. This direct one-pot protocol allows the synthesis of indoles with all easily available materials. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2551 / 2554

页数：4

共 50 条

[1] Copper-Catalyzed One-Pot Arylation and Cyclization of Diaryliodonium Salts Derived from o-Iodoanilines for Indolo[2,3-b]indoles Syntheses
Choi, Miseon
Mehra, Manish Kumar
Lee, Chung Whan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (04)
[2] Copper-catalyzed one-pot reactions of acetyl chloride, o-halobenzoic acids and Wittig reagents toward 3-methyl isocoumarin synthesis
Chen, Xuwen
Liu, Yunyun
RSC ADVANCES, 2017, 7 (60) : 37839 - 37843
[3] Copper-Catalyzed, C-C Coupling-Based One-Pot Tandem Reactions for the Synthesis of Benzofurans Using o-lodophenols, Acyl Chlorides, and Phosphorus Ylides
Liu, Yunyun
Wang, Hang
Wan, Jie-Ping
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10599 - 10604
[4] One-pot copper-catalyzed synthesis of 2-substituted benzothiazoles from 2-iodoanilines, benzyl chlorides and elemental sulfur
Yang, Zhao
Hu, Renhe
Li, Xiaotong
Wang, Xin
Gu, Ren
Han, Shiqing
TETRAHEDRON LETTERS, 2017, 58 (24) : 2366 - 2369
[5] Copper-catalyzed one-pot synthesis of alkynylphophonates
Song, Wang-Ze
Li, Jun-Hao
Li, Ming
He, Jun-Nan
Dong, Kun
Ullah, Karim
Zheng, Yu-Bin
SYNTHETIC COMMUNICATIONS, 2019, 49 (05) : 697 - 703
[6] One-Pot Synthesis of Benzene and Pyridine Derivatives via Copper-Catalyzed Coupling Reactions
Han, Jianwei
Guo, Xin
Liu, Yafeng
Fu, Yajie
Yan, Rulong
Chen, Baohua
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) : 2676 - 2681
[7] A One-Pot Copper-Catalyzed 3-Fold C-N Bond Coupling Strategy to the Synthesis of Substituted Benzimidazoles
Subramanian, Parthasarathi
Kaliappan, Krishna P.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (44) : 6915 - 6921
[8] Copper-Catalyzed One-Pot Synthesis of Substituted Benzimidazoles
Jin, Hongwei
Xu, Xiaoliang
Gao, Jianrong
Zhong, Jianhua
Wang, Yanguang
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 347 - 350
[9] Copper(I)-Catalyzed, One-Pot Synthesis of Multisubstituted Indoles from 2-Iodoanilines and Ethyl Buta-2,3-dienoate
Wang, Xianxue
Liu, Jin
Guo, Han
Ma, Chao
Gao, Xiai
Zhou, Kang
Huang, Guosheng
SYNTHESIS-STUTTGART, 2012, 44 (07): : 1037 - 1042
[10] One-Pot Synthesis of 4-Sulfonyliminotetrahydropyrimidin-2-one Derivatives through a Copper-Catalyzed Tandem Reaction
Tong, Tao
Wu, Xin
Li, Erfei
Kang, Honglan
Wang, Xiaoxia
Lv, Xin
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24) : 15533 - 15540

← 1 2 3 4 5 →