Polystyryl-BEMP as an efficient recyclable catalyst for the nucleophilic addition of nitroalkanes to α,β-unsaturated carbonyl compounds under solvent-free conditions

被引:38
作者
Ballini, R. [1 ]
Barboni, L. [1 ]
Castrica, L. [2 ]
Fringuelli, F. [2 ]
Lanari, D. [2 ]
Pizzo, F. [2 ]
Vaccaro, L. [2 ]
机构
[1] Univ Camerino, Dipartimento Sci Chim, Green Chem Grp, I-62032 Camerino, Italy
[2] Univ Perugia, Dipartimento Chim, Lab Green Synthet Organ Chem, CEMIN, I-06123 Perugia, Italy
关键词
BEMP; 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP); green chemistry; Michael addition; nitroalkanes; solid catalysts; solvent-free conditions;
D O I
10.1002/adsc.200800117
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
2-tert-Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene (PS-BEMP) is an efficient catalyst for the addition of nitroalkanes (1-1.5 equiv.) to alpha,beta-unsaturated carbonyl compounds (1.0 equiv.) in the absence of a reaction medium (solvent-free conditions). The corresponding gamma-nitro carbonyl compounds have been isolated in excellent yields but the catalyst can be satisfactorily recovered and used for only 3 times due to the magnetic stirring which caused crunching of the catalyst beads thus hampering its complete recovery. To optimize the catalyst's reuse and improve the environmental efficacy of solvent-free conditions, the first solvent-free cyclic continuous-flow reactor has been set up. This reactor has allowed the product to be isolated in an almost quantitative yield by using a very small amount of organic solvent, making the recovery and reuse of the catalyst efficient and reproducible.
引用
收藏
页码:1218 / 1224
页数:7
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