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噻吩并[3,2-]呋喃化合物的一锅法合成及性质研究

One-pot synthesis and property study on thieno[3,2-]furan compounds.

作者信息

Ma Weimin, Huang Jiawei, Li Chao, Jiang Yueren, Li Baolin, Qi Ting, Zhu Xiaozhang

机构信息

School of Chemical Sciences, University of Chinese Academy of Sciences Beijing 100049 P. R. China

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences Beijing 100190 P. R. China

出版信息

RSC Adv. 2019 Mar 1;9(13):7123-7127. doi: 10.1039/c9ra00796b.

DOI:10.1039/c9ra00796b
PMID:35519975
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9061063/
Abstract

Based on the regioselective intermolecular Suzuki coupling and subsequent intramolecular Ullmann C-O coupling reactions, one-pot synthesis of benzo[4,5]thieno[3,2-]benzofurans (BTBFs) was developed after optimization of the reaction conditions including catalysts, solvents, bases, ligands and reaction times. The one-pot reaction, with only 2 mol% Pd(PPh) and 2 mol% copper(i) thiophene-2-carboxylate (CuTc) as the catalysts, KPO·3HO as the base and -butanol as the solvent, afforded moderate to good yields (up to 70%) for a variety of substrates.

摘要

基于区域选择性分子间铃木偶联反应及随后的分子内乌尔曼碳-氧偶联反应,在对包括催化剂、溶剂、碱、配体和反应时间等反应条件进行优化后,开发了一锅法合成苯并[4,5]噻吩并[3,2-b]苯并呋喃(BTBFs)的方法。该一锅法反应仅使用2 mol%的Pd(PPh)和2 mol%的噻吩-2-羧酸铜(CuTc)作为催化剂,K₃PO₄·3H₂O作为碱,叔丁醇作为溶剂,对于多种底物可获得中等至良好的产率(高达70%)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/6d1ee65f397c/c9ra00796b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/1b5d6e59a104/c9ra00796b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/567a3e107a90/c9ra00796b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/6d1ee65f397c/c9ra00796b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/1b5d6e59a104/c9ra00796b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/567a3e107a90/c9ra00796b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d39d/9061063/6d1ee65f397c/c9ra00796b-f2.jpg

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本文引用的文献

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J Org Chem. 2017 Oct 20;82(20):10920-10927. doi: 10.1021/acs.joc.7b01745. Epub 2017 Sep 28.
2
Palladium-catalyzed benzofuran and indole synthesis by multiple C-H functionalizations.钯催化的多碳氢键官能团化合成苯并呋喃和吲哚
Chem Commun (Camb). 2017 Jun 16;53(49):6544-6556. doi: 10.1039/c7cc02053h.
3
Design and Functions of Semiconducting Fused Polycyclic Furans for Optoelectronic Applications.
二噻吩并呋喃的合成:在温和条件下通过级联铜催化的双C-S偶联和环化反应。
RSC Adv. 2021 Oct 21;11(54):34071-34078. doi: 10.1039/d1ra06881d. eCollection 2021 Oct 18.
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Copper-mediated construction of benzothieno[3,2-]benzofurans by intramolecular dehydrogenative C-O coupling reaction.铜介导的分子内脱氢C-O偶联反应构建苯并噻吩并[3,2-b]苯并呋喃
RSC Adv. 2021 Nov 10;11(57):36305-36309. doi: 10.1039/d1ra06985c. eCollection 2021 Nov 4.
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