Copper-Catalyzed Successive C-C bond formations on Indoles or Pyrrole: A Convergent Synthesis of Symmetric and Unsymmetric Hydroxyl Substituted N-H Carbazoles

被引：23

作者：

Qiao, Yu ^{[1
]}

Wu, Xin-Xing ^{[1
]}

Zhao, Yupeng ^{[1
]}

Sun, Yongqing ^{[1
]}

Li, Baoguo ^{[1
]}

Chen, Shufeng ^{[1
]}

机构：

[1] Inner Mongolia Univ, Coll Chem & Chem Engn, Inner Mongolia Key Lab Fine Organ Synth, Hohhot 010021, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 11期

基金：

中国国家自然科学基金;

关键词：

hydroxyl substituted N-H carbazoles; C-C bond formation; copper; indoles; pyrrole; HIGHLY EFFICIENT; SELECTIVE SYNTHESIS; 1ST SYNTHESIS; DERIVATIVES; HYDROACYLATION; BENZANNULATION; ALKALOIDS; MIGRATION; ALKYNES; FACILE;

D O I：

10.1002/adsc.201800154

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel copper-catalyzed successive C-Cbond formations on indoles and pyrrole approach for the direct synthesis of hydroxyl substituted N-H carbazoles is described. The current process represents an atom-economical method for the preparation of both symmetric and unsymmetric densely substituted and hydroxyl containing N-H carbazoles from easily accessible starting materials without the need for expensive metals and harsh reaction conditions.

引用

页码：2138 / 2143

页数：6

共 50 条

[21] Aerobic Synthesis of Substituted Quinoline from Aldehyde and Aniline: Copper-Catalyzed Intermolecular C-H Active and C-C Formative Cyclization
Yan, Rulong
Liu, Xingxing
Pan, Congming
Zhou, Xiaoqiang
Li, Xiaoni
Kang, Xing
Huang, Guosheng
ORGANIC LETTERS, 2013, 15 (18) : 4876 - 4879
[22] Copper-catalyzed Oxidative C-C, C-O, and C-N Bond Forming Reactions of Arylboronic Acids
Shirakawa, Eiji
Nishikawa, Ryo
Uchiyama, Nanase
Hata, Ippei
Hayashi, Tamio
CHEMISTRY LETTERS, 2013, 42 (03) : 269 - 271
[23] Rh(III)-Catalyzed Synthesis of N-Unprotected Indoles from Imidamides and Diazo Ketoesters via C-H Activation and C-C/C-N Bond Cleavage
Qi, Zisong
Yu, Songjie
Li, Xingwei
ORGANIC LETTERS, 2016, 18 (04) : 700 - 703
[24] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
Brasche, Gordon
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
[25] Intermolecular C-H Aminocyanation of Indoles via Copper-iodine Cocatalyzed Tandem C-N/C-C Bond Formation
Yu, Wenhua
Zhang, Xiaoxiang
Liu, Chenrui
Zhang, Yingying
Gu, Xiaoting
Liao, Jiahao
Zhang, Zhuan
Wei, Wanxing
Li, Guanghua
Liang, Taoyuan
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18) : 12424 - 12433
[26] Copper-Catalyzed N-H/C-H Sequential Relay Oxidative Radical Carboannulation: Construction of Diversely Substituted [60]Fullerene-Fused Tetrahydrocyclopenta[b]indoles
Liu, Tong-Xin
Wei, Juan
Zhang, Pengling
Ru, Yifei
Ma, Jinliang
Zhang, Xingjie
Ma, Nana
Zhang, Guisheng
ORGANIC LETTERS, 2019, 21 (16) : 6461 - 6465
[27] Palladium-Catalyzed Triple Successive C-H Functionalization: Direct Synthesis of Functionalized Carbazoles from Indoles
Verma, Akhilesh K.
Danodia, Abhinandan K.
Saunthwal, Rakesh K.
Patel, Monika
Choudhary, Deepak
ORGANIC LETTERS, 2015, 17 (15) : 3658 - 3661
[28] Direct Synthesis of N-H Carbazoles via Iridium(III)-Catalyzed Intramolecular C-H Amination
Suzuki, Chiharu
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
ORGANIC LETTERS, 2015, 17 (06) : 1597 - 1600
[29] Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: the direct synthesis of C2-functionalized indoles
Liu, Gang
Xu, Guangyang
Li, Jian
Ding, Dong
Sun, Jiangtao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (09) : 1387 - 1390
[30] A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp3 C-H Bond Activation Followed by C-C and C-O Bond Formation
Gogoi, Anupal
Guin, Srimanta
Rout, Saroj Kumar
Patel, Bhisma K.
ORGANIC LETTERS, 2013, 15 (08) : 1802 - 1805

← 1 2 3 4 5 →