Copper-Catalyzed Formal [4 + 1] Annulation toward Diverse Trifunctionalized Indolizines from Pyridinium 1,4-Zwitterionic Thiolates and Diazos

• DOI: 10.1021/acs.joc.3c00447
• Publication Date: 2023-05-12T10:09:11Z
• Authors: Wen Li; Hexiang Wang; Yuan Zhang; Limin Zhao; Pengfeng Guo; Hua Cao; Xiang Liu

Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- and sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium 1,4-zwitterionic thiolates and diazo compounds without any additives to access a library of trifunctionalized indolizines in good yields. Besides, isoquinolinium 1,4-zwitterionic thiolates and imidazolium 1,4-zwitterionic thiolates were also applied to this formal [4 + 1] annulation reaction. Of particular note is that various functional groups such as -CO2R, -CO2NR2, -CF3, -CN, and -(O)P(OR)2 could be easily introduced into cycloaddition products indolizines by this strategy.