Light triggered addition/annulation of 2-isocyanobiphenyls toward 6-trifluoromethyl-phenanthridines under photocatalyst-free conditions

被引:25
|
作者
Tang, Xiangyang [1 ]
Song, Shuang [1 ]
Liu, Cuibo [1 ,2 ]
Zhu, Rongjiao [1 ]
Zhang, Bin [1 ,2 ,3 ]
机构
[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China
[3] Tianjin Univ, Minist Educ, Key Lab Syst Bioengn, Tianjin 300072, Peoples R China
来源
RSC ADVANCES | 2015年 / 5卷 / 93期
基金
中国国家自然科学基金;
关键词
SILVER-MEDIATED TRIFLUOROMETHYLATION; C BOND FORMATION; OXIDATIVE CYCLIZATION; METAL-FREE; RADICAL TRIFLUOROMETHYLATION; PHENANTHRIDINE DERIVATIVES; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; ARYL ISONITRILES; ALKENES;
D O I
10.1039/c5ra16645d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A photocatalyst-free, light promoted sequential radical addition/annulation of 2-isocyanobiphenyls to 6-trifluoromethyl phenanthridines is presented. Wide substrate scopes and scale-up experiment demonstrate the promising efficiency and utility of this strategy.
引用
收藏
页码:76363 / 76367
页数:5
相关论文
共 46 条
  • [1] PhI(OAc)2-Mediated Synthesis of 6-(Trifluoromethyl)phenanthridines by Oxidative Cyclization of 2-Isocyanobiphenyls with CF3SiMe3 under Metal-Free Conditions
    Wang, Qile
    Dong, Xichang
    Xiao, Tiebo
    Zhou, Lei
    ORGANIC LETTERS, 2013, 15 (18) : 4846 - 4849
  • [2] Preparation of 6-Difluoromethylphosphonated Phenanthridines by Visible-Light-Driven Radical Cyclization of 2-Isocyanobiphenyls
    Wang, Shuang
    Jia, Wen-Liang
    Wang, Lin
    Liu, Qiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (31) : 6817 - 6821
  • [3] A photocatalyst-free method for the synthesis of 6-alkyl(aryl)phenanthridines under visible light irradiation
    Natarajan, Palani
    Partigya
    Pooja
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (47) : 22862 - 22868
  • [4] Synthesis of 6-substituted phenanthridines by metal-free, visible-light induced aerobic oxidative cyclization of 2-isocyanobiphenyls with hydrazines
    Xiao, Tiebo
    Li, Linyong
    Lin, Guoliang
    Wang, Qile
    Zhang, Ping
    Mao, Zong-wan
    Zhou, Lei
    GREEN CHEMISTRY, 2014, 16 (05) : 2418 - 2421
  • [5] Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with 2-isocyanobiphenyls to produce phenanthridines
    Gu, Lijun
    Jin, Cheng
    Liu, Jiyan
    Ding, Hongyan
    Fan, Baomin
    CHEMICAL COMMUNICATIONS, 2014, 50 (35) : 4643 - 4645
  • [6] Metal-Free Synthesis 6-Benzylphenanthridines via Radical Addition/Cyclization of 2-Isocyanobiphenyls
    Lu, Yuling
    Chen, Li
    Chen, Xia
    Yao, Meng
    Luo, Zengwei
    Zhang, Yonghui
    SYNTHESIS-STUTTGART, 2020, 52 (02): : 290 - 296
  • [7] Visible-light promoted dithioacetalization of aldehydes with thiols under aerobic and photocatalyst-free conditions
    Xing, Zhimin
    Yang, Mingyang
    Sun, Haiyu
    Wang, Zemin
    Chen, Peng
    Liu, Lin
    Wang, Xiaolei
    Xie, Xingang
    She, Xuegong
    GREEN CHEMISTRY, 2018, 20 (22) : 5117 - 5122
  • [8] Visible-light-promoted aerobic oxidative synthesis of β-ketosulfones under photocatalyst-free conditions
    Lv, Yufen
    Liu, Qishun
    Liu, Fei
    Yue, Huilan
    Li, Jiang-Sheng
    Wei, Wei
    TETRAHEDRON LETTERS, 2020, 61 (01)
  • [9] Photocatalyst-free Light-driven Dehydrogenation of Alcohols into Carbonyl Compounds under Mild Conditions
    Fan, Qiangwen
    Zhang, Honglei
    Ren, Huijun
    He, Yanling
    Gu, Yuhang
    Wu, Guorong
    Zhu, Haibo
    Xie, Zongbo
    Le, Zhanggao
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (17)
  • [10] Light-promoted oxidation of aldehydes to carboxylic acids under aerobic and photocatalyst-free conditions
    Batsika, Charikleia S.
    Koutsilieris, Charalampos
    Koutoulogenis, Giorgos S.
    Kokotou, Maroula G.
    Kokotos, Christoforos G.
    Kokotos, George
    GREEN CHEMISTRY, 2022, 24 (16) : 6224 - 6231