Visible light-mediated intramolecular C-H arylation of diazonium salts of N-(2-aminoaryl)benzoimines: a facile synthesis of 6-arylphenanthridines

被引:31
|
作者
Natarajan, Palani [1 ]
Kumar, Naveen
Sharma, Manjeet
机构
[1] Panjab Univ, Dept Chem, Chandigarh 160014, India
来源
ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 10期
关键词
TRANSITION-METAL-FREE; PHENANTHRIDINE DERIVATIVES; OXIDATIVE CYCLIZATION; PHOTOREDOX CATALYSIS; 2-ISOCYANOBIPHENYLS; FUNCTIONALIZATION; HETEROARENES; ISOCYANIDES; ISONITRILES; ACYLOXIMES;
D O I
10.1039/c6qo00275g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Utilizing [Ru(bpy)(3)]Cl-2 as a photoredox catalyst and a blue LED as an irradiation source, moderate to good yields of 6-arylphenanthridines were obtained from aryl diazonium salts in situ formed from the reactions of N-(2-aminoaryl) benzoimines and tert-butyl nitrite (tBuONO). Although few visible light-mediated protocols are available for the synthesis of 6-arylphenanthridines, this work provides a new method to access them readily from inexpensive and environmentally benign starting materials.
引用
收藏
页码:1265 / 1270
页数:6
相关论文
共 50 条
  • [1] Visible-Light-Mediated Monoselective Ortho C-H Arylation of 6-Arylpurine Nucleosides with Diazonium Salts
    Liang, Lei
    Xie, Ming-Sheng
    Wang, Hai-Xia
    Niu, Hong-Ying
    Qu, Gui-Rong
    Guo, Hai-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5966 - 5973
  • [2] Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts
    Hari, Durga Prasad
    Schroll, Peter
    Koenig, Burkhard
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) : 2958 - 2961
  • [3] Visible light mediated synthesis of 6H-benzo[c]chromenes: transition-metal-free intramolecular direct C-H arylation
    Heredia, Micaela D.
    Puiatti, Marcelo
    Rossi, Roberto A.
    Buden, Maria E.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 20 (01) : 228 - 239
  • [4] Metal-free, C-H arylation of indole and its derivatives with aryl diazonium salts by visible-light photoredox catalysis
    Zhang, Ying-Peng
    Feng, Xiao-Long
    Yang, Yun-Shang
    Cao, Bi-Xia
    TETRAHEDRON LETTERS, 2016, 57 (21) : 2298 - 2302
  • [5] Asymmetric Synthesis of Planar Chiral Ferrocenes by Enantioselective Intramolecular C-H Arylation of N-(2-Haloaryl)ferrocenecarboxamides
    Liu, Lantao
    Zhang, An-An
    Zhao, Rui-Juan
    Li, Feng
    Meng, Tuan-Jie
    Ishida, Naoki
    Murakami, Masahiro
    Zhao, Wen-Xian
    ORGANIC LETTERS, 2014, 16 (20) : 5336 - 5338
  • [6] Visible light-mediated direct C8-H arylation of quinolines and C2-H arylation of quinoline-N-oxides and pyridines under organic photocatalysis
    Banu, Saira
    Singh, Kuldeep
    Yadav, Prem P.
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (04) : 1481 - 1488
  • [7] Visible-Light-Driven Synthesis of Phenanthridin-6(5H)-one and N-Substituted Carbazole Derivatives through Intramolecular C-H Arylation
    Cuellar, Micaela Ayelen
    Heredia, Micaela Denise
    Brarda, Guillermo
    Barolo, Silvia Maricel
    Vazquez, Eva Daniela Diaz
    Uberman, Paula Marina
    Martin, Sandra Elizabeth
    Buden, Maria Eugenia
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (38)
  • [8] Visible light-driven C-H arylation of heteroarenes with aryl diazonium salts in water catalyzed by a Z-scheme CuInS2/K-C3N4 heterojunction
    Liu, Qian-Hui
    Kang, Shi-Long
    Cui, Zhen-Shui
    Liu, Yu-Heng
    Zhang, Mo
    Zhang, Zhan-Hui
    GREEN CHEMISTRY, 2024, 26 (08) : 4803 - 4810
  • [9] Visible Light Photoredox-Catalyzed Direct C-H Arylation of Quinoxalin-2(1H)-ones with Diaryliodonium Salts
    Samanta, Raj K.
    Meher, Prahallad
    Murarka, Sandip
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 10947 - 10957
  • [10] Palladium-catalyzed intramolecular C-H arylation of 2-halo-N-Boc-N-arylbenzamides for the synthesis of N-H phenanthridinones
    Hu, Quan-Fang
    Gao, Tian-Tao
    Shi, Yao-Jie
    Lei, Qian
    Yu, Luo-Ting
    RSC ADVANCES, 2018, 8 (25) : 13879 - 13890