Davenport Chemical Research Laboratories Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
School of Science and Institute of Scientific Research, Great Bay University, Dongguan 523000, China.
Chem Commun (Camb). 2023 Apr 18;59(32):4770-4773. doi: 10.1039/d3cc01139a.
Prompted by the recent stepwise mechanistic proposal for the Huisgen [3+2] cycloaddition reaction between enamine and α-diazo ester, where the nucleophilic addition of the enamine carbon onto the terminal nitrogen of diazo ester is crucial, we examined the possible use of N-heterocyclic olefins (NHOs) as highly electron-rich dipolarophiles in these reactions. The mesoionic NHOs derived from 1,2,3-triazoles undergo fast [4+1] cycloaddition to give 3-(triazolium-4-yl)-(3)-pyrazol-4-olates at room temperature. The reaction mechanism has been explored through experimental and DFT computational studies.
受最近关于烯胺和α-重氮酯之间的Huisgen [3+2]环加成反应的逐步机制提议的启发，其中烯胺碳对重氮酯末端氮的亲核加成是关键的，我们研究了 N-杂环烯烃（NHOs）作为这些反应中高电子富二极体的可能用途。 衍生自 1,2,3-三唑的中氮杂环烯烃在室温下快速进行[4+1]环加成，得到 3-(三唑并-4-基)-(3)-吡唑-4-醇盐。 通过实验和 DFT 计算研究探讨了反应机理。
