Regioselective Synthesis of the Tetrahydrocarbazole Core of Akuammiline Alkaloids via Palladium-Catalyzed Intramolecular Arylation Reaction

被引:0
|
作者
Vampugani, Naga M. R. [1 ]
Shelke, Ajay B. [1 ]
Singh, Prashant B. [1 ]
Ahmad, Asrar [1 ]
Kapat, Ajoy [1 ]
机构
[1] Shiv Nadar Inst Eminence Deemed Univ, Sch Nat Sci, Dept Chem, Delhi NCR, Greater Noida 201314, Uttar Pradesh, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 07期
关键词
PROTON-ABSTRACTION MECHANISM; H BOND FUNCTIONALIZATION; SEMIPINACOL REARRANGEMENT; ANNULATED HETEROCYCLES; AMINATION;
D O I
10.1021/acs.joc.3c02619
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tetrahydrocarbazole is the central core for several biologically active alkaloids, and regioselective synthesis of this core is a challenging task. Herein, we report an efficient strategy for the synthesis of this core involving palladium-catalyzed intramolecular arylation reaction with excellent regioselectivity (>99%) starting from N-phenyl-bromoalkene without having any relocation of double bonds via competitive palladium-catalyzed isomerization reaction. Broad functional group tolerance and exclusive regioselectivity have been observed for meta-substituted halide substrates. Furthermore, this reaction can be scalable on the gram scale.
引用
收藏
页码:4461 / 4466
页数:6
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