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

共 50 条

[31] Synthesis of novel azole-fused quinazolines via one-pot, sequential Ullmann-type coupling and intramolecular dehydrogenative C-N bonding
Nandwana, Nitesh Kumar
Pericherla, Kasiviswanadharaju
Kaswan, Pinku
Kumar, Anil
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2947 - 2950
[32] Diastereoselective Oxidative C-N/C-O and C-N/C-N Bond Formation Tandems Initiated by Visible Light: Synthesis of Fused N-Arylindolines
Morris, Scott A.
Nguyen, Theresa H.
Zheng, Nan
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2311 - 2316
[33] Progress in Photochemical and Electrochemical C-N Bond Formation for Urea Synthesis
Song, Hakhyeon
Haro, Danae A. Chipoco
Huang, Po-Wei
Barrera, Luisa
Hatzell, Marta C.
ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (21) : 2944 - 2953
[34] One-Pot Ullmann C-N Coupling Cyclization Toward Domino Synthesis of Fused Hexacyclic Quinolinotriazoloacridinones Catalyzed by CuI/L-Proline
Jin, Rong-Zhang
Li, Yu-Ling
Wang, Xiang-Shan
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) : 986 - 992
[35] Soluble N-substituted poly(benzimidazole imide)s via C-N coupling reaction
Shang, Zhenfang
Yang, Li
Chang, Guanjun
POLYMER INTERNATIONAL, 2016, 65 (03) : 332 - 338
[36] Synthesis of (-)-Epi-Indolactam V by an Intramolecular Buchwald-Hartwig C-N Coupling Cyclization Reaction
Mari, Michele
Bartoccini, Francesca
Piersanti, Giovanni
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15): : 7727 - 7734
[37] Synthesis of Double Benzimidazole-Fused Quinazolines and Pyrimidines Catalyzed by Recyclable Magnetic Cu-MOF-74
Lee, Seong Weon
Dao, Pham Duy Quang
Cho, Chan Sik
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (47)
[38] C-N coupling with cobalt
West, Thomas
NATURE SYNTHESIS, 2024, 3 (10): : 1186 - 1186
[39] Synthesis of high Tg and organosoluble poly(N-arylene benzimidazole ether imide) copolymers by C-N/C-O coupling reaction
Sidra, Lala Rukh
Mushtaq, Nafeesa
Chen, Guofei
Fang, Xingzhong
HIGH PERFORMANCE POLYMERS, 2018, 30 (04) : 465 - 474
[40] Rh(III)-Catalyzed C-C/C-N Coupling of Imidates with α-Diazo Imidamide: Synthesis of Isoquinoline-Fused Indoles
Wang, He
Li, Lei
Yu, Songjie
Li, Yunyun
Li, Xingwei
ORGANIC LETTERS, 2016, 18 (12) : 2914 - 2917

← 1 2 3 4 5 →