Green protocol for conjugate addition of Thiols to α,β-Unsaturated ketones using a [Bmim]PF6/H2O system

被引:160
作者
Yadav, JS [1 ]
Reddy, BVS [1 ]
Baishya, G [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1021/jo034335l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha,beta-Unsaturated ketones undergo conjugate addition rapidly with thiols in a hydrophobic ionic liquid [bmim]PF6/H2O solvent system (2:1) in the absence of any acid catalyst to afford the corresponding Michael adducts in high to quantitative yields with excellent 1,4-selectivity under mild and neutral conditions. The enones show enhanced reactivity in ionic liquids, thereby reducing reaction times and improving the yields significantly. The use of ionic liquids helps to avoid the use of either acid or base catalysts for this conversion. The recovered ionic liquid was reused four to five times with consistent activity.
引用
收藏
页码:7098 / 7100
页数:3
相关论文
共 27 条
[1]   A natural phosphate and doped-catalyzed Michael addition of mercaptans to α,β-unsaturated carbonyl compounds [J].
Abrouki, Y ;
Zahouily, M ;
Rayadh, A ;
Bahlaouan, B ;
Sebti, S .
TETRAHEDRON LETTERS, 2002, 43 (49) :8951-8953
[2]  
[Anonymous], CHIROTECHNOLOGIES IN
[3]   Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].
Bandini, M ;
Cozzi, PG ;
Giacomini, M ;
Melchiorre, P ;
Selva, S ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704
[4]   FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].
CLARK, JH .
CHEMICAL REVIEWS, 1980, 80 (05) :429-452
[5]   A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations [J].
Emori, E ;
Arai, T ;
Sasai, H ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4043-4044
[6]  
FLUHARTY AL, 1974, CHEM THIOL GROUP 2, P589
[7]   TUMOR INHIBITORS HAVING POTENTIAL FOR INTERACTION WITH MERCAPTO ENZYMES AND-OR COENZYMES - REVIEW [J].
FUJITA, E ;
NAGAO, Y .
BIOORGANIC CHEMISTRY, 1977, 6 (03) :287-309
[8]   New developments in catalysis using ionic liquids [J].
Gordon, CM .
APPLIED CATALYSIS A-GENERAL, 2001, 222 (1-2) :101-117
[9]  
HELDER R, 1977, TETRAHEDRON LETT, P2181
[10]   ADDITION OF AROMATIC THIOLS TO CONJUGATED CYCLOALKENONES, CATALYZED BY CHIRAL BETA-HYDROXY AMINES - A MECHANISTIC STUDY ON HOMOGENEOUS CATALYTIC ASYMMETRIC-SYNTHESIS [J].
HIEMSTRA, H ;
WYNBERG, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (02) :417-430