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

被引：4

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

页码：7988 / 7997

页数：10

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