关键词: Deoxy-Breslow Intermediate N-Heterocyclic Carbenes Organocatalysis Pyridinium Substrates Umpolung

Mesh : Alkylation Catalysis Heterocyclic Compounds / chemistry Methane / analogs & derivatives chemistry

来  源:   DOI:10.1002/anie.202117524   PDF(Pubmed)

Abstract:
Umpolung N-heterocyclic carbene (NHC) catalysis of non-aldehyde substrates offers new pathways for C-C bond formation, but has proven challenging to develop in terms of viable substrate classes. Here, we demonstrate that pyridinium ions can undergo NHC addition and subsequent intramolecular C-C bond formation through a deoxy-Breslow intermediate. The alkylation demonstrates, for the first time, that deoxy-Breslow intermediates are viable for catalytic umpolung of areniums.
摘要:
非醛底物的UmpolungN-杂环卡宾(NHC)催化为C-C键形成提供了新的途径,但已证明在可行的底物类别方面具有挑战性。这里,我们证明吡啶离子可以通过脱氧-Breslow中间体进行NHC加成和随后的分子内C-C键形成。烷基化表明,第一次,脱氧-Breslow中间体可用于催化增强芳烃。
公众号