Rasta Resin-DMAP and its Use as a Recyclable Catalyst for the Addition of Carbon Dioxide to Epoxides

Abstract

Rasta resin-DMAP, a new heterogeneous polystyrene-based amine, has been synthesized and used as a catalyst in addition reactions of carbon dioxide to epoxides to afford cyclic carbonate products. This new material was found to be a more efficient catalyst than divinyl benzene cross-linked polystyrene-supported DMAP, and was readily recovered and reused without significant loss of catalytic activity.

Key words

polymer-supported organocatalyst - polystyrene - DMAP - carbon dioxide - cyclic carbonate

References and Notes

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Teng, Y.; Toy, P. H. Synlett 2011, 551.

17

See Supporting Information for details.

18

General Procedure for CO ₂ Addition Reactions
Epoxide 7a-j (22.4 mmol), CH₂Cl₂ (0.5 mmol), and 4 (0.224 mmol) were placed in a 25 mL stainless-steel autoclave. Carbon dioxide was then introduced into the reactor at an initial pressure of 20 bar at r.t. The reactor was then heated to 120 ˚C, and the pressure was adjusted to 30 bar. The reaction mixture was stirred under these conditions for the indicated time, and then the autoclave was cooled using an ice bath. After releasing the pressure, compound 4 was filtered off and washed with CH₂Cl₂. The filtrate was concentrated in vacuo to afford the product 8a-j. The identity of the products was confirmed by ^¹H NMR.