Kabachnik-Fields and Prins-Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study
| Authors | |
|---|---|
| Year of publication | 2015 |
| Type | Article in Periodical |
| Magazine / Source | J Chem Applications |
| MU Faculty or unit | |
| Citation | |
| Web | http://www.avensonline.org/wp-content/uploads/JCAP-02-2380-5021-0004.pdf |
| Field | Organic chemistry |
| Keywords | alpha-Aminophosphonates; 4-Amidotetrahydropyranes; Metal catalysis; Polymer supported Ce(III); Solid support catalysis |
| Description | 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 alpha-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weak acid 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 alpha-aminophosphonates, and 4-amidotetrahydropyrane derivatives. |
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