C-N Coupling via Antiaromatic Endocyclic Nitrenium Ions

被引：22

作者：

Bera, Shyamal Kanti ^{[1
]}

Alam, Md Toufiqe ^{[1
]}

Mal, Prasenjit ^{[1
]}

机构：

[1] HBNI, NISER, Sch Chem Sci, PO Bhimpur Padanpur,Via Jatni, Bhubaneswar 752050, Odisha, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

关键词：

BENZIMIDAZOLE-FUSED PHENANTHRIDINES; LASER FLASH-PHOTOLYSIS; ONE-POT SYNTHESIS; AROMATIC-SUBSTITUTION; BOND FORMATION; 2-ARYLBENZIMIDAZOLES; AMINATION; ARENES;

D O I：

10.1021/acs.joc.9b01921

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a C-N coupling reaction via antiaromatic endocyclic nitrenium ions. The nitrenium ion intermediate was generated by a combination of iodine(III) reagent PhI(OCOCF3)(2) and the N-H center of benzimidazole units at ambient laboratory conditions. Metal-free synthesis of benzimidazole-fused phenanthridine derivatives was achieved in good to excellent yields.

引用

页码：12009 / 12020

页数：12

共 46 条

[1] Pyrrolo[1,2-f]phenanthridines and related non-rigid analogues as antiviral agents
Almerico, AM
Mingoia, F
Diana, P
Barraja, P
Montalbano, A
Lauria, A
Loddo, R
Sanna, L
Delpiano, D
Setzu, MG
Musiu, C
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (01) : 3 - 10
[2] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature
Antonchick, Andrey P.
Samanta, Rajarshi
Kulikov, Katharina
Lategahn, Jonas
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8605 - 8608
[3] Iodine(III)-Enabled Distal C-H Functionalization of Biarylsulfonanilides
Bal, Ankita
Maiti, Saikat
Mal, Prasenjit
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (18) : 11278 - 11287
[4] Borodkin G. I., 2008, RUSS CHEM REV, V77, P395, DOI DOI 10.1070/RC2008V077N05ABEH003760
[5] A Platinum(II) Phenylphenanthroimidazole with an Extended Side-Chain Exhibits Slow Dissociation from a c-Kit G-Quadruplex Motif
Castor, Katherine J.
Liu, Zhaomin
Fakhoury, Johans
Hancock, Mark A.
Mittermaier, Anthony
Moitessier, Nicolas
Sleiman, Hanadi F.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (52) : 17836 - 17845
[6] Conversion of sterically hindered diacylated 1,2-phenylenediamines into 2-substituted benzimidazoles
Charton, J
Girault-Mizzi, S
Sergheraert, C
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (05) : 492 - 497
[7] Modular Synthesis of Benzimidazole-Fused Phenanthridines from 2-Arylbenzimidazoles and o-Dibromoarenes by a Palladium-Catalyzed Cascade Process
Chen, Chunxia
Shang, Guoning
Zhou, Jingjie
Yu, Yanhan
Li, Bin
Peng, Jinsong
[J]. ORGANIC LETTERS, 2014, 16 (07) : 1872 - 1875
[8] Reactions of N-methyl-N-(4-biphenylyl)nitrenium ion with electron-rich arenes:: Laser flash photolysis and product studies
Chiapperino, D
McIlroy, S
Falvey, DE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) : 3567 - 3577
[9] N-Heterocyclic Nitrenium Ligands: A Missing Link Explored
Choudhury, Joyanta
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (46) : 10772 - 10774
[10] Hexafluoroisopropanol as a highly versatile solvent
Colomer, Ignacio
Chamberlain, Anna E. R.
Haughey, Maxwell B.
Donohoe, Timothy J.
[J]. NATURE REVIEWS CHEMISTRY, 2017, 1 (11)

← 1 2 3 4 5 →