Basic-functionalized recyclable ionic liquid catalyst: A solvent-free approach for Michael addition of 1,3-dicarbonyl compounds to nitroalkenes under ultrasound irradiation

被引:28
作者
Narayanaperumal, Senthil [1 ]
da Silva, Rodrigo Cesar [1 ]
Feu, Karla Santos [1 ]
de la Torre, Alexander Fernandez [1 ]
Correa, Arlene G. [1 ]
Paixao, Marcio Weber [1 ]
机构
[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Task specific ionic liquids; Michael addition; Recyclability; Ultrasonication; 1,3-Dicarbonyl compounds; REUSABLE CATALYST; EFFICIENT; ORGANOCATALYSTS; IMIDAZOLIUM; AMMONIUM; 2,4-PENTANDIONE; ACETYLACETONE; CHALCONES; THIOUREAS; KETONES;
D O I
10.1016/j.ultsonch.2012.11.002
中图分类号
O42 [声学];
学科分类号
070206 ; 082403 ;
摘要
A task-specific ionic liquid (TSIL) has been introduced as a recyclable catalyst in Michael addition. A series of nitroalkenes and various C-based nucleophiles were reacted in the presence of 30 mol% of recyclable basic-functionalized ionic liquid. Good to excellent yields were obtained in 30 min under ultrasound irradiation. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:793 / 798
页数:6
相关论文
共 80 条
[1]   Michael reactions promoted by η1-O-enolatoruthenium(II) complexes derived from Ru(cod)(cot), diphosphine, and dimethyl malonate [J].
Alvarez, SG ;
Hasegawa, S ;
Hirano, M ;
Komiya, S .
TETRAHEDRON LETTERS, 1998, 39 (29) :5209-5212
[2]  
Anastas P.T., 1998, Green Chemistry: Frontiers in Benign Chemical Synthesis and Process
[3]   Chemistry of pyrazino[2,1-b]quinazoline-3,6-diones [J].
Avendaño, C ;
Menéndez, JC .
CURRENT ORGANIC CHEMISTRY, 2003, 7 (02) :149-173
[4]  
BADAWI AM, 1983, CURR SCI INDIA, V52, P1169
[5]   Tetrahydropyran Synthesis by Intramolecular Conjugate Addition to Enones: Synthesis of the Clavosolide Tetrahydropyran Ring [J].
Bates, Roderick W. ;
Song, Ping .
SYNTHESIS-STUTTGART, 2010, (17) :2935-2942
[6]   Ionic liquids and chirality: opportunities and challenges [J].
Baudequin, C ;
Baudoux, J ;
Levillain, J ;
Cahard, D ;
Gaumont, AC ;
Plaquevent, JC .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093
[7]   P-BEMP: A new efficient and commercially available user-friendly and recyclable heterogeneous organocatalyst for the Michael addition of 1,3-dicarbonyl compounds [J].
Bensa, D ;
Constantieux, T ;
Rodriguez, J .
SYNTHESIS-STUTTGART, 2004, (06) :923-927
[8]  
Bergman E., 1959, ORG REACT, V10, P179, DOI DOI 10.1002/0471264180.OR010.03
[9]   Addition of hydrogen sulfide to methyl acrylate over solid basic catalysts [J].
Breysse, E ;
Fajula, F ;
Finiels, A ;
Frémy, G ;
Tichit, D ;
Moreau, C .
JOURNAL OF CATALYSIS, 2005, 233 (02) :288-296
[10]   The Growing Impact of Catalysis in the Pharmaceutical Industry [J].
Busacca, Carl A. ;
Fandrick, Daniel R. ;
Song, Jinhua J. ;
Senanayake, Chris H. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1825-1864