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
  • [21] Visible-light-induced intramolecular sp3 C-H oxidation of 2-alkyl-substituted benzamides for the synthesis of functionalized iminoisobenzofurans
    Wu, Lingang
    Hao, Yanan
    Liu, Yuxiu
    Wang, Qingmin
    CHEMICAL COMMUNICATIONS, 2019, 55 (92) : 13908 - 13911
  • [22] Visible-light-driven copper(<sc>ii</sc>) catalysis for 2,3-disubstituted quinazolinone synthesis via Ullmann N-arylation and C-H oxidative amidation
    Abdulghaffar, Ahmed Th.
    Hu, Pei
    Hu, Yifan
    Liu, Chenxu
    Ren, Yanrong
    Cao, Zhongyan
    Xu, Yuanqing
    Jiang, Min
    Xu, Hao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025,
  • [23] CuI/I2-Mediated Intramolecular Oxidative Cyclization Reaction of N-(2-pyridyl)amidines by the Direct Double C-H Functionalization of a C(sp3)-H Bond
    Yi, Fengping
    Zhang, Songxing
    Zhang, Lirong
    Yi, Weiyin
    Yu, Rui
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (12) : 1808 - 1817
  • [24] Synthesis of Indolo[2,3-c]quinolin-6(7H)-ones and Antimalarial Isoneocryptolepine. Computational Study on the Pd-Catalyzed Intramolecular C-H Arylation
    Szabo, Timea
    Papp, Marcell
    Nemeth, Dora Rita
    Dancso, Andras
    Volk, Balazs
    Milen, Matyas
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 128 - 145
  • [25] C-H arylation reactions through aniline activation catalysed by a PANI-g-C3N4-TiO2 composite under visible light in aqueous medium
    Wang, Liang
    Shen, Jun
    Yang, Sen
    Liu, Wenjie
    Chen, Qun
    He, Mingyang
    GREEN CHEMISTRY, 2018, 20 (06) : 1290 - 1296
  • [26] Visible-light-induced indole synthesis via intramolecular C-N bond formation: desulfonylative C(sp2)-H functionalization
    Li, Quanzhe
    Gu, Xintao
    Wei, Yin
    Shi, Min
    CHEMICAL SCIENCE, 2022, 13 (39) : 11623 - 11632
  • [27] Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C-H Arylation Reactions
    Cerna, Igor
    Pohl, Radek
    Klepetarova, Blanka
    Hocek, Michal
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22): : 9048 - 9054
  • [28] Facile Fabrication of Bi2MoO6/g-C3N4 Heterojunction Nanosheets: Facile Synthesis and Enhanced Visible Light Photocatalytic Property
    Su, Fu
    Huang, Jianshu
    Xu, Yanhua
    SCIENCE OF ADVANCED MATERIALS, 2023, 15 (07) : 905 - 914
  • [29] Visible light-mediated, rose Bengal-catalyzed oxidative radical C-H cyclization of alkyl 1,1′-biaryl-2-ones: An efficient synthesis of 10-alkylphenanthren-9-ols in water
    Natarajan, Palani
    Kumar, Naveen
    Chaudhary, Renu
    Venugopalan, Paloth
    TETRAHEDRON LETTERS, 2020, 61 (18)
  • [30] Nanoporous g-C3N4 nanosheets: Facile synthesis and excellent visible-light photocatalytic H2 evolution performance
    Shu, Zhu
    Xie, Cong
    Zhou, Jun
    Li, Tiantian
    Chen, Ying
    Wang, Wenbin
    Tan, Yigen
    Zhao, Zhengliang
    JOURNAL OF ALLOYS AND COMPOUNDS, 2018, 747 : 140 - 148