Basic ionic liquid as catalysis and reaction medium:: A novel and green protocol for the markovnikov addition of N-heterocycles to vinyl esters, using a task-specific ionic liquid, [bmIm]OH

被引:125
作者
Xu, JM [1 ]
Liu, BK [1 ]
Wu, WB [1 ]
Qian, C [1 ]
Wu, Q [1 ]
Lin, XF [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
D O I
10.1021/jo0600914
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide ([bmIm]OH), has been introduced as a catalyst and reaction medium for the Markovnikov addition of N-heterocycles to vinyl esters under mild conditions. The evidence for the role of this basic ionic liquid [bmIm]OH in promoting the Markovnikov addition has been given. On the basis of the evidence, a mechanism was postulated.
引用
收藏
页码:3991 / 3993
页数:3
相关论文
共 45 条
[21]   THROMBOXANE SYNTHETASE INHIBITORS (TXSI) - DESIGN, SYNTHESIS, AND EVALUATION OF A NOVEL SERIES OF OMEGA-PYRIDYLALKENOIC ACIDS [J].
KATO, K ;
OHKAWA, S ;
TERAO, S ;
TERASHITA, Z ;
NISHIKAWA, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (03) :287-294
[22]   Cleavage of aromatic methyl ethers by chloroaluminate ionic liquid reagents [J].
Kemperman, GJ ;
Roeters, TA ;
Hilberink, PW .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) :1681-1686
[23]   Microwave-assisted preparation of 1-butyl-3-methylimidazolium tetrachlorogallate and its catalytic use in acetal formation under mild conditions [J].
Kim, YJ ;
Varma, RS .
TETRAHEDRON LETTERS, 2005, 46 (43) :7447-7449
[24]   Converting exo-selective Diels-Alder reaction to endo-selective in chloroloaluminate ionic liquids [J].
Kumar, A ;
Pawar, SS .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1419-1420
[25]   Catalysis - A greener solution [J].
Leitner, W .
NATURE, 2003, 423 (6943) :930-931
[26]   A mild esterification process in phosphonium salt ionic liquid [J].
McNulty, J ;
Cheekoori, S ;
Nair, JJ ;
Larichev, V ;
Capretta, A ;
Robertson, AJ .
TETRAHEDRON LETTERS, 2005, 46 (21) :3641-3644
[27]   Preparation of C9-aldehyde via aldol condensation reactions in ionic liquid media [J].
Mehnert, CP ;
Dispenziere, NC ;
Cook, RA .
CHEMICAL COMMUNICATIONS, 2002, (15) :1610-1611
[28]   Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmlm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles [J].
Ranu, BC ;
Banerjee, S .
ORGANIC LETTERS, 2005, 7 (14) :3049-3052
[29]   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 [J].
Ranu, BC ;
Dey, SS .
TETRAHEDRON, 2004, 60 (19) :4183-4188
[30]   Catalysis by ionic liquid.: A green protocol for the stereoselective debromination of vicinal-dibromides by [pmIm]BF4 under microwave irradiation [J].
Ranu, BC ;
Jana, R .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8621-8624