DMAP-catalyzed cascade reaction: one-pot synthesis of benzofurans in water

被引:48
作者
Shang, Yongjia [1 ]
Wang, Cuie [1 ]
He, Xinwei [1 ]
Ju, Kai [1 ]
Zhang, Min [1 ]
Yu, Shuyan [1 ]
Wu, Jiaping [1 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Minist Educ, Key Lab Funct Mol Solids,Anhui Key Lab Mol Based, Wuhu 241000, Peoples R China
基金
中国国家自然科学基金;
关键词
Benzofuran; Cascade reaction; Dimethylaminopyridine; Halogenated ketones; Salicylaldehydes; ORGANIC-REACTIONS; PALLADIUM; HALIDES; ALKYNES; ENOLATE; ROUTE; RINGS;
D O I
10.1016/j.tet.2010.09.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of benzofurans were efficiently synthesized in good to excellent yields using 4-dimethylaminopyridine (DMAP) catalyzed cascade reaction between salicylaldehydes and halogenated ketones in water at 80 degrees C opened atmosphere. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
引用
收藏
页码:9629 / 9633
页数:5
相关论文
共 43 条
[1]   Straightforward synthesis of perhydrofuro[2,3-b]furans through a Wacker-type reaction [J].
Alonso, Francisco ;
Sanchez, Daniel ;
Soler, Tatiana ;
Yus, Miguel .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (13) :2118-2126
[2]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[3]  
ANNIINA E, 2007, CHEM REV, V107, P5416
[4]  
ANNIINA E, 2006, J ORG CHEM, V71, P2538
[5]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6]   MASS-SPECTRAL AND ANTI-MICROBIAL STUDIES OF THE BENZOFURAN ANALOG OF CHLORAMPHENICOL [J].
BEVINAKATTI, HS ;
BADIGER, VV .
ARCHIV DER PHARMAZIE, 1981, 314 (02) :162-167
[7]   Water in organocatalytic processes: Debunking the myths [J].
Blackmond, Donna G. ;
Armstrong, Alan ;
Coombe, Vyv ;
Wells, Andrew .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3798-3800
[8]   Enamine-based aldol organocatalysis in water: Are they really "all wet"? [J].
Brogan, Andrew P. ;
Dickerson, Tobin J. ;
Janda, Kim D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8100-8102
[9]   Palladium catalysis in the construction of the benzo[b]furan and furan rings from alkynes and organic halides or triflates [J].
Cacchi, S ;
Fabrizi, G ;
Goggiomani, A .
HETEROCYCLES, 2002, 56 (1-2) :613-632
[10]   Axially chiral NHC-Pd(II) complexes in the oxidative kinetic resolution of secondary alcohols using molecular oxygen as a terminal oxidant [J].
Chen, Tao ;
Jiang, Jia-Jun ;
Xu, Qin ;
Shi, Min .
ORGANIC LETTERS, 2007, 9 (05) :865-868