Unexpected side reactions of imidazolium-based ionic liquids in the base-catalysed Baylis-Hillman reaction

被引：215

作者：

Aggarwal, VK ^{[1
]}

Emme, I ^{[1
]}

Mereu, A ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 15期

关键词：

D O I：

10.1039/b203079a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Low yields are obtained when the Baylis-Hillman reaction is conducted in the presence of an imidazolium-based ionic liquid due to direct addition of the deprotonated imidazolium salt to the aldehyde. Ionic liquids are evidently not inert.

引用

页码：1612 / 1613

页数：2

共 27 条

[1] Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated
Aggarwal, VK
Dean, DK
Mereu, A
Williams, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) : 510 - 514
[2] Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implications
Aggarwal, VK
Mereu, A
[J]. CHEMICAL COMMUNICATIONS, 1999, (22) : 2311 - 2312
[3] Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction
Aggarwal, VK
Mereu, A
Tarver, GJ
McCague, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) : 7183 - 7189
[4] STABLE CARBENES AS STRONG BASES
ALDER, RW
ALLEN, PR
WILLIAMS, SJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) : 1267 - 1268
[5] A STABLE DIAMINOCARBENE
ARDUENGO, AJ
GOERLICH, JR
MARSHALL, WJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) : 11027 - 11028
[6] Arduengo AJ, 1997, LIEBIGS ANN-RECL, P365
[7] Stable carbenes
Bourissou, D
Guerret, O
Gabbaï, FP
Bertrand, G
[J]. CHEMICAL REVIEWS, 2000, 100 (01) : 39 - 91
[8] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS
BRESLOW, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) : 3719 - 3726
[9] The Heck reaction in ionic liquids: A multiphasic catalyst system
Carmichael, AJ
Earle, MJ
Holbrey, JD
McCormac, PB
Seddon, KR
[J]. ORGANIC LETTERS, 1999, 1 (07) : 997 - 1000
[10] DUGAS H, 1989, BIORGANIC CHEM, pH576

← 1 2 3 →