Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

We described results of comparative studies of the application of Ce(III) cation supported on macroporous weakly acidic polyacrylate resin as catalyst in two model three-component domino syntheses, i.e. Kabachnik-Fields domino synthesis of α-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weakacid macroporous cation-exchanger shown in the studied reactions at least the same or better catalytic activity as salt CeCl3.7H2O, eventually doped by NaI. Further, we found that reactivity of the low reactive 4-methoxybenzaldehyde as carbonyl compounds in the presence of Ce(III) catalyst increases, while the reactivity of the highly reactive 4-nitrobenzaldehyde in this case strongly decreases due to its low coordination with the catalyst. Finally, the presented synthetic protocols using cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses of α-aminophosphonates, and 4-amidotetrahydropyrane derivatives.