Catalysis by ionic liquid: a simple, green and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br

被引:137
作者
Ranu, BC [1 ]
Dey, SS [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India
关键词
Michael addition; thiol; thiophosphate; ionic liquid; green catalysis;
D O I
10.1016/j.tet.2004.03.052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A room temperature ionic liquid, 1-pentyl-3-methylimidazolium bromide, [pmIm]Br efficiently catalyzes Michael addition of thiols and diethyl dithiophosphate to a variety of conjugated alkenes such as alpha,beta-unsaturated carbonyl compounds, carboxylic esters, nitriles and chalcones without requiring any other organic solvent and catalyst. The ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4183 / 4188
页数:6
相关论文
共 42 条
[31]  
SHELDON RA, 1993, CHROTECHNOLOGIES IND
[32]   Bismuth nitrate-catalyzed versatile Michael reactions [J].
Srivastava, N ;
Banik, BK .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2109-2114
[33]  
Su C, 2003, SYNTHESIS-STUTTGART, P555
[34]  
UENO Y, 1981, SYNTHESIS-STUTTGART, P547
[35]  
Wabnitz TC, 2003, SYNLETT, P1070
[36]   Room-temperature ionic liquids. Solvents for synthesis and catalysis [J].
Welton, T .
CHEMICAL REVIEWS, 1999, 99 (08) :2071-2083
[37]   Green protocol for conjugate addition of Thiols to α,β-Unsaturated ketones using a [Bmim]PF6/H2O system [J].
Yadav, JS ;
Reddy, BVS ;
Baishya, G .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7098-7100
[38]   OsO4 in ionic liquid [Bmim]PF6:: A recyclable and reusable catalyst system for olefin dihydroxylation.: Remarkable effect of DMAP [J].
Yao, QW .
ORGANIC LETTERS, 2002, 4 (13) :2197-2199
[39]   Fluorapatite: efficient catalyst for the Michael addition [J].
Zahouily, M ;
Abrouki, Y ;
Rayadh, A ;
Sebti, S ;
Dhimane, H ;
David, M .
TETRAHEDRON LETTERS, 2003, 44 (12) :2463-2465
[40]   Na2CaP2O7, a new catalyst for Michael addition [J].
Zahouily, M ;
Abrouki, Y ;
Rayadh, A .
TETRAHEDRON LETTERS, 2002, 43 (43) :7729-7730