Reverse Regioselective Cp*Co(III)-Catalyzed [4 + 2] C–H Annulation of N-Chloroamides with Vinylsilanes: Synthesis of 4-Silylated Isoquinolones and Their Synthetic Utilities
废止
化学
区域选择性
催化作用
烷基化
乙烯
乙烯基硅烷
立体化学
有机化学
组合化学
药物化学
作者
Arijit Ghosh,Tamanna Rana,Nilanjan Bhaduri,Amit B. Pawar
出处
期刊:Organic Letters [American Chemical Society] 日期:2023-10-23卷期号:25 (43): 7878-7883被引量:1
We have developed a Cp*Co(III)-catalyzed reverse regioselective [4 + 2] annulation of N-chlorobenzamides/acrylamides with vinylsilanes for the synthesis of 4-silylated isoquinolones. The reaction was performed at ambient temperature under redox-neutral conditions. The reaction utilized the N-Cl bond as an internal oxidant, furnished the required products with excellent regioselectivities, and demonstrated high functional group tolerance. The synthetic utility of 4-silylated isoquinolones has been demonstrated for the preparation of 4-heteroarylated and 4-alkylated isoquinolones via metal-free C-C couplings. Additionally, 3,4-dihydroisoquinolones were synthesized via protodesilylation of 4-silylated isoquinolones, thus making vinylsilane an ethylene surrogate.