Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions

被引:8
作者
Gimbert, Carolina [1 ]
Vallribera, Adelina [1 ]
Gladysz, John A. [2 ]
Jurisch, Markus [3 ,4 ]
机构
[1] Univ Autonoma Barcelona, Dept Chem, Cerdanyola Del Valles 08193, Spain
[2] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
[3] Univ Erlangen Nurnberg, Inst Organ Chem, D-91054 Erlangen, Germany
[4] Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat, D-91054 Erlangen, Germany
关键词
ASYMMETRIC REDUCTION; CATALYSIS; SOLVENTS; IMINES;
D O I
10.1016/j.tetlet.2010.06.136
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The fluorous phosphines P[(CH2)(m)R-fn](3) (R-fn = (CF2)(n-1)CF3; m/n = 2/8, 3/8, 3/10) are efficient nucleophilic catalysts of Michael addition reactions. They can be easily recycled based upon their highly temperature-dependent solubilities (thermomorphism), with recovery by simple liquid/solid phase separation. The phosphonium salt formed by reaction of the nucleophilic phosphine with the alpha,beta-unsaturated system appears to be a significant component of the catalyst rest state. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4662 / 4665
页数:4
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