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.
Polystyryl-BEMP as an Efficient Recyclable Catalyst for the Nucleophilic Addition of Nitroalkanes to a,b-Unsaturated Carbonyl Compounds under Solvent-Free Conditions
VACCARO, Luigi;CASTRICA, Luca;FRINGUELLI, Francesco;LANARI, DANIELA;PIZZO, Ferdinando
2008
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.