Baylis-Hillman reaction in [bdmim][[PF6] ionic liquid

被引:98
作者
Hsu, JC [1 ]
Yen, YH [1 ]
Chu, YH [1 ]
机构
[1] Natl Chung Cheng Univ, Dept Chem & Biochem, Chiayi 621, Taiwan
关键词
Baylis-Hillman reaction; ionic liquid;
D O I
10.1016/j.tetlet.2004.04.099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new use of ionic liquid [bdmim][PF6] as solvent for the Baylis-Hillman reaction is presented. Unlike the commonly used [bmim][PF6] that evidently reacts with electrophilic aldehydes under basic conditions, ionic liquid [bdmim][PF6] is inert and the Baylis-Hillman reaction in [bdmim][PF6] proceeds smoothly with better yield. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4673 / 4676
页数:4
相关论文
共 20 条
[1]   Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope [J].
Aggarwal, VK ;
Emme, I ;
Fulford, SY .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :692-700
[2]   Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated [J].
Aggarwal, VK ;
Dean, DK ;
Mereu, A ;
Williams, R .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :510-514
[3]   Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications [J].
Aggarwal, VK ;
Mereu, A .
CHEMICAL COMMUNICATIONS, 1999, (22) :2311-2312
[4]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[5]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[6]  
Cammarata L, 2001, PHYS CHEM CHEM PHYS, V3, P5192, DOI 10.1039/b106900d
[7]  
FITTON AO, 1989, J CHEM RES-S, P337
[8]  
Fraga-Dubreuil J., 2000, TETRAHEDRON LETT, V41, P7351
[9]   Room temperature ionic liquids of alkylimidazolium cations and fluoroanions [J].
Hagiwara, R ;
Ito, Y .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 105 (02) :221-227
[10]   FUNCTIONALIZATION OF THE ALPHA-POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL-COMPOUNDS - HIGHLY PRESSURE-DEPENDENT REACTIONS [J].
HILL, JS ;
ISAACS, NS .
TETRAHEDRON LETTERS, 1986, 27 (41) :5007-5010