A regenerable immobilized nadh model IV: Reduction of pyridine-2-carbaldehyde by immobilized 1,4-dihydronicotinamide in the presence of Mg2+ ions

Dihydronicotinamide, anchored to a macroreticular polystyrene resin, reduces pyridine-2-carbaldehyde (PCA) in the presence of Mg²⁺ ions in acetonitrile. The reactions are clean at room temperature, the high rate precluding complications arising from slow side reactions. The influence of Mg²⁺ concentration on the rate of reduction of PCA by polymer-bound reagent and BNAH (1-benzyl-1,4-dihydronicotinamide; low-molar-mass analog) has been studied. Analysis of the kinetic data showed that of the processes contributing to the overall reduction, the reaction between the reductant and the complexed substrate proceeded at the highest rate. In the polymer-bound reagent, “site isolation” on the rigid matrix was observed to prevent bimolecular disproportionation of the neighboring dihydronicotinamides. Regeneration of the polymeric reagent was achieved with an efficiency of 98% per cycle.