A photocatalyst-free method for the synthesis of 6-alkyl(aryl)phenanthridines under visible light irradiation

被引：8
作者：
Natarajan, Palani [1 ,2 ]
Partigya [1 ,2 ]
Pooja [1 ,2 ]
机构：
[1] Panjab Univ, Dept Chem, Chandigarh 160014, India
[2] Panjab Univ, Ctr Adv Studies Chem, Chandigarh 160014, India
来源：
NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 47期
关键词：
PHOTOREDOX CATALYSIS; PHENANTHRIDINE DERIVATIVES; H ARYLATION; ISOCYANIDES; CYCLIZATION; ANNULATION; COMPLEXES; ALKALOIDS; CHLORIDES; ALKYNES;
D O I：
10.1039/d2nj04414e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel and effective blue LED-induced methodology has been developed to synthesize a number of 6-alkyl(aryl)phenanthridines from isocyanobiaryls and alkyl(aryl)sulfinates in ethyl lactate under aerobic conditions. This protocol did not require a photoredox catalyst, and the reaction was sparked by the photochemical activity of an electron donor-acceptor complex formed by the interaction of isocyanobiaryls with alkyl(aryl)sulfinates. The environmental friendliness, mildness, gram-scale synthesizability, lack of toxic organic solvents/additives, and lack of a transition metal are only a few notable advantages of this methodology.
引用
收藏
页码：22862 / 22868
页数：7
相关论文
共 53 条
  • [1] N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes
    Allen, Laura J.
    Cabrera, Pablo J.
    Lee, Melissa
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) : 5607 - 5610
  • [2] Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source
    An, Xiao-De
    Yu, Shouyun
    [J]. ORGANIC LETTERS, 2015, 17 (20) : 5064 - 5067
  • [3] Phenanthridine derivatives as promising new anticancer agents: synthesis, biological evaluation and binding studies
    Azad, Iqbal
    Ahmad, Rumana
    Khan, Tahmeena
    Saquib, Mohammad
    Hassan, Firoj
    Akhter, Yusuf
    Khan, Abdul R.
    Nasibullah, Malik
    [J]. FUTURE MEDICINAL CHEMISTRY, 2020, 12 (08) : 709 - 739
  • [4] Visible Light Photoredox Activation of Sulfonyl Chlorides: Applications in Organic Synthesis
    Chaudhary, Renu
    Natarajan, Palani
    [J]. CHEMISTRYSELECT, 2017, 2 (22): : 6458 - 6479
  • [5] Visible light photoredox-controlled reactions of N-radicals and radical ions
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) : 2044 - 2056
  • [6] Synthesis of Polysubstituted Phenanthridines via Ligand-Free Copper-Catalyzed Annulation
    Chen, Yan-Fu
    Hsieh, Jen-Chieh
    [J]. ORGANIC LETTERS, 2014, 16 (17) : 4642 - 4645
  • [7] Regiospecific Synthesis of 1-Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion
    Cheng, Yuanzheng
    Yuan, Xiangai
    Jiang, Heng
    Wang, Ruzhi
    Ma, Jing
    Zhang, Yan
    Yu, Shouyun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2859 - 2866
  • [8] Oxidative homodimerization of substituted olefins by DDQ visible light photocatalysis
    Chuskit, Deachen
    Chaudhary, Renu
    Venugopalan, Paloth
    Koenig, Burkhard
    Natarajan, Palani
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (24): : 3553 - 3556
  • [9] Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes
    Crisenza, Giacomo E. M.
    Mazzarella, Daniele
    Melchiorre, Paolo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) : 5461 - 5476
  • [10] Phytochemical and biological investigations of Amaryllidaceae alkaloids: a review
    Ding, Yan
    Qu, Dan
    Zhang, Kai-Mei
    Cang, Xiao-Xin
    Kou, Zi-Nong
    Xiao, Wei
    Zhu, Jing-Bo
    [J]. JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2017, 19 (01) : 53 - 100
123456