A Photochemical Intramolecular C-N Coupling Toward the Synthesis of Benzimidazole-Fused Phenanthridines

被引：20

作者：

Bera, Shyamal Kanti ^{[1
]}

Boruah, Palash J. ^{[2
]}

Parida, Shraddha Saraswati ^{[1
]}

Paul, Amit K. ^{[2
]}

Mal, Prasenjit ^{[1
]}

机构：

[1] HBNI, Sch Chem Sci, Natl Inst Sci Educ & Res NISER, Jatni 752050, Odisha, India

[2] Natl Inst Technol Meghalaya, Dept Chem, Shillong 793003, Meghalaya, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 14期

关键词：

METAL-FREE; 2-ARYLBENZIMIDAZOLES; AMINATION; BORYLATION; ARYLATION; CATALYST;

D O I：

10.1021/acs.joc.1c00871

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a direct photochemical dehydrogenative C-N coupling of unactivated C(sp(2))-H and N(sp(2))-H bonds. The catalysts or additive-free transformation of 2-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazole to benzo[4,5]imidazo[1,2-f]phenanthiidine was achieved at, similar to 350 nm of irradiation via epsilon-hydrogen abstraction. DFT calculations helped to understand that the N-H center dot center dot center dot pi interaction was essential for the reaction to proceed at a lower energy than expected.

引用

页码：9587 / 9602

页数：16

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