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Journal Articles Advanced Synthesis and Catalysis Year : 2021

Organocatalytic Synthesis of Substituted Vinylene Carbonates

Abstract

The organocatalytic synthesis of substituted 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 substituted 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).
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Dates and versions

hal-03821278 , version 1 (20-10-2022)

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Killian Onida, Alice J Haddleton, Sébastien Norsic, Christophe Boisson, Franck d'Agosto, et al.. Organocatalytic Synthesis of Substituted Vinylene Carbonates. Advanced Synthesis and Catalysis, 2021, 363 (22), pp.5129-5137. ⟨10.1002/adsc.202100870⟩. ⟨hal-03821278⟩
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