Rhodium-Catalyzed Synthesis of 2-Methylindoles via C-N Bond Cleavage of N-Allylbenzimidazole

被引：1
|
作者：
Biswal, Pragati [1 ,2 ]
Nanda, Tanmayee [1 ,2 ]
Prusty, Namrata [1 ,2 ]
Mohanty, Smruti Ranjan [1 ,2 ]
Ravikumar, Ponneri C. [1 ,2 ]
机构：
[1] Natl Inst Sci Educ & Res NISER Bhubaneswar, Sch Chem Sci, Jatni 752050, Orissa, India
[2] Homi Bhabha Natl Inst HBNI, Training Sch Complex, Mumbai 400094, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 13期
关键词：
DIAZO-COMPOUNDS; H ALKENYLATION; INDOLES; DERIVATIVES; CYCLIZATION; ALKYLATION; ALLYLATION; AMINES;
D O I：
10.1021/acs.joc.2c03048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rhodium-catalyzed oxidative C-H/N-H dehydrogenative[3 + 2] annulation strategy has been reported between anilines and N-allylbenzimidazole for the synthesis of 2-methylindolescaffolds. An N-allylbenzimidazole has been usedas a 2C synthon for the synthesis of indole, and more importantly,this transformation involves the cleavage of the thermodynamicallystable C-N bond of allylamine. Detailed mechanistic studieshave been performed and a key intermediate was detected in HRMS. Thistransformation proceeds through a cascade of C(sp(2))-Hallylation followed by intramolecular cyclization.
引用
收藏
页码：7988 / 7997
页数：10
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