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Organocatalytic synthesis of vinylene carbonates
Organocatalytic synthesis of vinylene carbonates
- Publication Year :
- 2021
- Publisher :
- Cambridge University Press (CUP), 2021.
-
Abstract
- The organocatalytic synthesis of vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90°C under solvent-free conditions. A wide range of vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20-99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (> 30 g after 5 runs).
Details
- Database :
- OpenAIRE
- Accession number :
- edsair.doi...........dca9164f7ae5bc8d4f2e0b11e2681550
- Full Text :
- https://doi.org/10.33774/chemrxiv-2021-mm08f