N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

被引:323
作者
Grasa, GA [1 ]
Kissling, RM [1 ]
Nolan, SP [1 ]
机构
[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
关键词
D O I
10.1021/ol0264760
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.
引用
收藏
页码:3583 / 3586
页数:4
相关论文
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 [J].
Aggarwal, VK ;
Dean, DK ;
Mereu, A ;
Williams, R .
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 [J].
Aggarwal, VK ;
Mereu, A .
CHEMICAL COMMUNICATIONS, 1999, (22) :2311-2312
[3]  
Arduengo AJ, 1999, HELV CHIM ACTA, V82, P2348, DOI 10.1002/(SICI)1522-2675(19991215)82:12<2348::AID-HLCA2348>3.0.CO
[4]  
2-M
[5]   First example of N-heterocyclic carbenes as catalysts for living polymerization:: Organocatalytic ring-opening polymerization of cyclic esters [J].
Connor, EF ;
Nyce, GW ;
Myers, M ;
Möck, A ;
Hedrick, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :914-915
[6]  
DSa BA, 1996, J ORG CHEM, V61, P2963
[7]  
Enders D, 2002, ANGEW CHEM INT EDIT, V41, P1743, DOI 10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO
[8]  
2-Q
[9]  
Greene T. W., 1999, PROTECTIVE GROUPS OR
[10]   Stereoelectronic effects characterizing nucleophilic carbene ligands bound to the Cp*RuCl (Cp* = η5-C5Me5) moiety:: A structural and thermochemical investigation [J].
Huang, JK ;
Schanz, HJ ;
Stevens, ED ;
Nolan, SP .
ORGANOMETALLICS, 1999, 18 (12) :2370-2375