A simple and green procedure for the conjugate addition of thiols to conjugated alkenes employing polyethylene glycol (PEG) as an efficient recyclable medium

被引:64
作者
Kamal, A [1 ]
Reddy, DR [1 ]
Rajendar [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
conjugate addition; Thiols; conjugated alkenes; polyethylene glycol;
D O I
10.1016/j.tetlet.2005.09.082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polyethylene glycol (PEG) is found to be an inexpensive, nontoxic, environmentally friendly reaction medium for the conjugate addition of thiols to conjugated alkenes to afford the corresponding adducts in excellent yields under mild and neutral conditions. Products of undesirable side reactions resulting from polymerization are not observed. The use of PEG avoids the use of either acid or base catalysts for this conversion and moreover PEG can be recovered and reused. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7951 / 7953
页数:3
相关论文
共 51 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]   Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].
Alam, MM ;
Varala, R ;
Adapa, SR .
TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119
[3]  
Anastas P. T., 1998, GREEN CHEM THEORY PR
[4]  
Anastas P.T., 1996, GREEN CHEM DESIGNING, DOI [10.1021/bk-1996-0626, DOI 10.1021/BK-1996-0626]
[5]  
Anastas P. T., 1998, GREEN CHEM FRONTIERS
[6]  
[Anonymous], POLY ETHYLENE GLYCOL
[7]  
[Anonymous], CHIROTECHNOLOGIES IN
[8]   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
[9]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[10]   Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility [J].
Cave, GWV ;
Raston, CL ;
Scott, JL .
CHEMICAL COMMUNICATIONS, 2001, (21) :2159-2169