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
[1]   The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids [J].
Aggarwal, A ;
Lancaster, NL ;
Sethi, AR ;
Welton, T .
GREEN CHEMISTRY, 2002, 4 (05) :517-520
[2]  
ATTARYAN OS, 1988, ZH ORG KHIM+, V24, P1339
[3]   Sequence specificity, reactivity, and antitumor activity of DNA-alkylating pyrrole-imidazole diamides [J].
Bando, T ;
Iida, H ;
Tao, ZF ;
Narita, A ;
Fukuda, N ;
Yamori, T ;
Sugiyama, H .
CHEMISTRY & BIOLOGY, 2003, 10 (08) :751-758
[4]  
BELOUSOV AM, 1980, ZH ORG KHIM+, V16, P2622
[5]   Green processing using ionic liquids and CO2 [J].
Blanchard, LA ;
Hancu, D ;
Beckman, EJ ;
Brennecke, JF .
NATURE, 1999, 399 (6731) :28-29
[6]   FRIEDEL CRAFTS REACTIONS IN AMBIENT-TEMPERATURE MOLTEN-SALTS [J].
BOON, JA ;
LEVISKY, JA ;
PFLUG, JL ;
WILKES, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :480-483
[7]   Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide [J].
Brown, RA ;
Pollet, P ;
McKoon, E ;
Eckert, CA ;
Liotta, CL ;
Jessop, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1254-1255
[8]   Process development of voriconazole: A novel broad-spectrum triazole antifungal agent [J].
Butters, M ;
Ebbs, J ;
Green, SP ;
MacRae, J ;
Morland, MC ;
Murtiashaw, CW ;
Pettman, AJ .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (01) :28-36
[9]   Proton affinities of N-heterocyclic carbene super bases [J].
Chen, H ;
Justes, DR ;
Cooks, RG .
ORGANIC LETTERS, 2005, 7 (18) :3949-3952
[10]   Mechanism and conditions for highly enantioselective epoxidation of α,β-enones using charge-accelerated catalysis by a rigid quaternary ammonium salt [J].
Corey, EJ ;
Zhang, FY .
ORGANIC LETTERS, 1999, 1 (08) :1287-1290