A three-component iodine-catalyzed oxidative coupling reaction: a heterodifunctionalization of 3-methylindoles

被引：3

作者：

Zhang, Wei ^{[1
,2
]}

Xiang, Shiqun ^{[2
]}

Fan, Weibin ^{[2
]}

Jin, Jiang ^{[2
]}

Li, Yinghua ^{[2
]}

Huang, Deguang ^{[1
,2
]}

机构：

[1] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350007, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 26期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; ELECTRON-RICH HETEROCYCLES; FRIEDEL-CRAFTS ALKYLATION; METAL-FREE SULFENYLATION; 3-SUBSTITUTED INDOLES; 2,3-DISUBSTITUTED INDOLES; CONTROLLABLE SYNTHESIS; PHOTOREDOX CATALYSIS; CARBONYL-COMPOUNDS; ALPHA;

D O I：

10.1039/d1ob00730k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free method for the synthesis of heterodifunctional indole derivatives is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated by the TBHP/KI catalytic system, enabling the direct realization of the heterodifunctionalization of indole in one pot. The product of this reaction is a novel heterodifunctional compound. This work might provide a new effective method for the synthesis of polycyclic indole compounds.

引用

页码：5794 / 5799

页数：6

共 50 条

[31] Trichloromethyl-Radical-Initiated Three-Component Reaction of Alkenes with CHCl3 and Quinoxalinones
Wu, Yechun
Zhang, Jie
Yu, Jin-Tao
Pan, Changduo
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (05) : 687 - 692
[32] Direct Enantioselective Three-Component Kabachnik-Fields Reaction Catalyzed by Chiral Bis(imidazoline)-Zinc(II) Catalysts
Ohara, Mutsuyo
Nakamura, Shuichi
Shibata, Norio
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) : 3285 - 3289
[33] Synthesis of functionalized γ-lactones via a three-component cascade reaction catalyzed by consecutive N-heterocyclic carbene systems
Zhao, Qian
Han, Bo
Wang, Biao
Leng, Hai-Jun
Peng, Cheng
Huang, Wei
RSC ADVANCES, 2015, 5 (34): : 26972 - 26976
[34] Synergistic Brønsted Base/Photoredox-Catalyzed Three-Component Coupling with Malonates to Synthesize δ-Hydroxy Esters and δ-Keto Esters
Li, Ting
Wang, Wei
Dong, Ming
Zhang, Zhijie
Yu, Sha
Chen, Zhengchu
Wei, Siping
Yi, Dong
CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (09) : 957 - 962
[35] One-Pot Three-Component Coupling Reaction of α-Amino Aryl Ketones, Indoles, and Perbromomethane Under Mild Conditions
Chen, De
Lu, Hao
Liu, Yuxuan
Deng, Wei
Qiu, Renhua
Xiang, Jiannan
FRONTIERS IN CHEMISTRY, 2022, 10
[36] Nickel-Catalyzed Three-Component Cross-Electrophile Coupling of 1,3-Dienes with Aldehydes and Aryl Bromides
Qi, Ya-Qiong
Liu, Shuai
Xu, Yan
Li, Yang
Su, Tong
Ni, Hai-Liang
Gao, Yuanji
Yu, Wenhao
Cao, Peng
Hu, Ping
Zhao, Ke-Qing
Wang, Bi-Qin
Chen, Bin
ORGANIC LETTERS, 2022, 24 (28) : 5023 - 5028
[37] Novel One-pot Three-component Coupling Reaction with Trimethylsilylmethylphosphonate, Acyl Fluoride, and Aldehyde through the Horner-Wadsworth-Emmons Reaction
Umezawa, Taiki
Seino, Tomoya
Matsuda, Fuyuhiko
ORGANIC LETTERS, 2012, 14 (16) : 4206 - 4209
[38] Copper-Catalyzed Three-Component Formal [3+1+2] Benzannulation for Carbazole and Indole Synthesis
Guo, Tenglong
Han, Li
Wang, Tingpeng
Lei, Lan
Zhang, Jian
Xu, Dezhu
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14) : 9117 - 9128
[39] Indium(III) chloride catalyzed three-component coupling reaction: A novel synthesis of 2-substituted aryl(indolyl)kojic acid derivatives as potent antifungal and antibacterial agents
Reddy, B. V. Subba
Reddy, M. Ramana
Madan, Ch.
Kumar, K. Pranay
Rao, M. Srinivasa
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (24) : 7507 - 7511
[40] An Expedient Synthesis of β-Acetamido- and β-Benzamidocarbonyl Compounds via KAl(SO4)2•12H2O-catalyzed Three-component Coupling Reaction
Molla, Aniruddha
Hussain, Sahid
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2013, 45 (06) : 494 - 503

← 1 2 3 4 5 →