Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization | |
Department | OSSO国家重点实验室 |
Liu, Changhui1; Zhou, Li1; Huang, Wenbo1; Wang, Man1; Gu YL(顾彦龙)1,2; Gu YL(顾彦龙) | |
2016 | |
Source Publication | Advanced Synthesis and Catalysis |
ISSN | 1615-4150 |
Volume | 358Issue:6Pages:900-918 |
Abstract | An effective method to synthesize -functionalized furan and pyrrole derivatives was developed using 2-alkoxy-2,3-dihydrofurans as modular precursors. This protocol featured a previously unreported tandem nucleophilic substitution/heteroaromatization reaction. Nucleophiles such as indole, -oxoketene dithioacetal, trimethoxybenzene, and dimethoxynaphthalene can react readily with 2-alkoxy-2,3-dihydrofurans to afford -functionalized five-membered ring heterocycles in the presence of acid catalysts, such as copper bromide and iron chloride. The mechanism of the reaction was also discussed, in which the first step, nucleophilic substitution, is the key in triggering the succeeding heteroaromatization. This method can also be extended to the synthesis of dihydrothiophenes. |
Keyword | Dihydrothiophenes Furans Heteroaromatization Indoles Pyrroles Alpha-oxoketene Dithioacetal |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1002/adsc.201500993 |
Funding Organization | National Natural Science Foundation of China (21173089;21373093);the fundamental research funds for the central universities in China (2014ZZGH019);the Cooperative Innovation Center of Hubei Province |
Indexed By | SCI |
If | 5.646 |
Language | 英语 |
compositor | 第二作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/19984 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Gu YL(顾彦龙) |
Affiliation | 1.HUST, Sch Chem & Chem Engn, Hubei Key Lab Mat Chem & Serv Failure,Minist Educ, Key Lab Mat Chem Energy Convers & Storage, 1037 Luoyu Rd, Wuhan 430074, Peoples R China 2.Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China |
Recommended Citation GB/T 7714 | Liu, Changhui,Zhou, Li,Huang, Wenbo,et al. Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization[J]. Advanced Synthesis and Catalysis,2016,358(6):900-918. |
APA | Liu, Changhui,Zhou, Li,Huang, Wenbo,Wang, Man,Gu YL,&顾彦龙.(2016).Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization.Advanced Synthesis and Catalysis,358(6),900-918. |
MLA | Liu, Changhui,et al."Synthesis of Furans and Pyrroles from 2-Alkoxy-2,3-dihydrofurans Through a Nucleophilic Substitution-Triggered Heteroaromatization".Advanced Synthesis and Catalysis 358.6(2016):900-918. |
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LZ01028954 .pdf(717KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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