Polystyryl-BEMP as an efficient recyclable catalyst for the nucleophilic addition of nitroalkanes to α,β-unsaturated carbonyl compounds under solvent-free conditions
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Ballini, R.
[1
]
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Barboni, L.
[1
]
Castrica, L.
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Univ Perugia, Dipartimento Chim, Lab Green Synthet Organ Chem, CEMIN, I-06123 Perugia, ItalyUniv Camerino, Dipartimento Sci Chim, Green Chem Grp, I-62032 Camerino, Italy
Castrica, L.
[2
]
Fringuelli, F.
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Univ Perugia, Dipartimento Chim, Lab Green Synthet Organ Chem, CEMIN, I-06123 Perugia, ItalyUniv Camerino, Dipartimento Sci Chim, Green Chem Grp, I-62032 Camerino, Italy
Fringuelli, F.
[2
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Lanari, D.
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Univ Perugia, Dipartimento Chim, Lab Green Synthet Organ Chem, CEMIN, I-06123 Perugia, ItalyUniv Camerino, Dipartimento Sci Chim, Green Chem Grp, I-62032 Camerino, Italy
Lanari, D.
[2
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Pizzo, F.
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Univ Perugia, Dipartimento Chim, Lab Green Synthet Organ Chem, CEMIN, I-06123 Perugia, ItalyUniv Camerino, Dipartimento Sci Chim, Green Chem Grp, I-62032 Camerino, Italy
Pizzo, F.
[2
]
Vaccaro, L.
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Univ Perugia, Dipartimento Chim, Lab Green Synthet Organ Chem, CEMIN, I-06123 Perugia, ItalyUniv Camerino, Dipartimento Sci Chim, Green Chem Grp, I-62032 Camerino, Italy
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
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.