Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans

被引：4

作者：

Chen, Xingyu ^{[1
,2
]}

Lu, Sixian ^{[1
,2
]}

Deng, Ping ^{[3
]}

Chang, Xiaoqiang ^{[1
,2
]}

Zhao, Yifan ^{[1
,2
]}

Ma, Yue ^{[1
,2
]}

Zhang, Dong ^{[1
,2
]}

Xia, Fei ^{[1
,2
]}

Yang, Lan ^{[1
,2
]}

Wang, Jigang ^{[1
,2
]}

Sun, Peng ^{[1
,2
]}

机构：

[1] Acad Chinese Med Sci, Inst Chinese Mat Med, Beijing 100700, Peoples R China

[2] Acad Chinese Med Sci, Artemisinin Res Ctr, Beijing 100700, Peoples R China

[3] Chongqing Univ, Sch Pharm, Chongqing 400016, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 01期

基金：

中国国家自然科学基金;

关键词：

benzofuran; 1; 3-dicarbonyl compounds; divergent catalysis; indoles; QIKs; ENANTIOSELECTIVE ALPHA-ARYLATION; ASYMMETRIC DIELS-ALDER; DEAROMATIZATION; CONSTRUCTION; MONOACETALS; ANNULATION; EXCHANGE; NITROGEN;

D O I：

10.1002/adsc.202100607

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance.

引用

页码：94 / 102

页数：9

共 21 条

[21] Synthesis of α\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$\upalpha $$\end{document}-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles
Stanley N. S. Vasconcelos
Evelin Fornari
Ignez Caracelli
Hélio A. Stefani
Molecular Diversity, 2017, 21 (4) : 893 - 902

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