An Intramolecular Radical C-N Coupling by N -Iodosuccinimide

被引：5

作者：

Bera, Shyamal Kanti ^{[1
]}

Bhanja, Rosalin ^{[1
]}

Sahu, Chandan Chittapriya ^{[1
]}

Mal, Prasenjit ^{[1
]}

机构：

[1] Natl Inst Sci Educ & Res NISER, OCC Homi Bhabha Natl Inst, Sch Chem Sci, PO Bhimpur Padanpu,Via Jatni, Bhubaneswar 752050, Odisha, India

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 04期

关键词：

benzimidazole-fused phenanthridines; C-N coupling; TFE; N; -iodosuccinimide; radical cyclization; BENZIMIDAZOLE-FUSED PHENANTHRIDINES; 2-ARYLBENZIMIDAZOLES;

D O I：

10.1055/a-2063-0221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A useful method for the formation of benzimidazole-fused phenanthridines through an intramolecular coupling of unactivated C(sp2)-H and N(sp3)-H bonds using N-iodosuccinimide (NIS) in trifluoroethanol (TFE) is presented. The synthesis of benzo[4,5]imidazo[1,2f]phenanthridines from 2-([1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazole derivatives is mild, efficient, and sustainable, with high yields and minimal waste generation. The control experiments and EPR studies were aimed at rationalizing the radical pathway of the reaction. Specifically, the use of 1,1-diphenylethylene, TEMPO, BHT, and DMPO as a free -radical spin-trapping reagent in EPR studies, allowed us to conceive a radical pathway. The gram-scale synthesis further supported the practical utility of the methodology for the field of synthetic chemistry.

引用

页码：585 / 596

页数：12

共 46 条

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