O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo- or Thermal-Induced N-O Cleavage in C(sp2) C(sp3) Bond Formation

被引:37
作者
Xia, Peng-Ju [1 ]
Hu, Yuan-Zhuo [1 ]
Ye, Zhi-Peng [1 ]
Li, Xu-Jie [1 ]
Xiang, Hao-Yue [1 ]
Yang, Hua [1 ,2 ]
机构
[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China
[2] Cent South Univ, Key Lab Hunan Prov Water Environm & Agr Prod Safe, Changsha 410083, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H CYANOALKYLATION; VISIBLE-LIGHT; FACILE ACCESS; QUINOXALIN-2(1H)-ONES; CYCLIZATION; GENERATION; ALKENES; ARYLATION; CATALYSTS; CASCADE;
D O I
10.1021/acs.joc.9b03251
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
O-Perfluoropyridin-4-yl group was first installed onto cycloketone oximes as a new electrophore, which was proven to be efficient iminyl radical precursors under photocatalytic and thermal conditions. A range of O-perfluoropyridin-4-yl oximes were successfully utilized in C(sp(2))-C(sp(3)) bond formations of quinoxalin-2(1H)-ones and alkenes, providing facile accesses to a range of functionalized alkylnitriles.
引用
收藏
页码:3538 / 3547
页数:10
相关论文
共 16 条
  • [11] Metal-free, visible-light-induced C(sp2)-H functionalization/C-O bond formation for the synthesis of flavones using air as an oxidant
    Bai, Yuntao
    Yang, Manqiang
    Lin, Shao-Xia
    Borse, Rahul Anil
    Thoke, Mahesh Bhagwan
    Yuan, Daqiang
    TETRAHEDRON LETTERS, 2023, 121
  • [12] Anchoring of a Copper(II)-Schiff Base Complex onto Silica-Coated Ferrite Nanoparticles: A Magnetically Separable Catalyst for Oxidative C-O Coupling by Direct C(sp2)-H and C(sp3)-H Bond Activation
    Ghanbaripour, Rashid
    Samadizadeh, Marjaneh
    Honarpisheh, Golnaz
    Abdolmohammadi, Majid
    SYNLETT, 2015, 26 (15) : 2117 - 2120
  • [13] Iron-Catalysed Remote C(sp3)-H Azidation of O-Acyl Oximes and N-Acyloxy Imidates Enabled by 1,5-Hydrogen Atom Transfer of Iminyl and Imidate Radicals: Synthesis of γ-Azido Ketones and β-Azido Alcohols
    Torres-Ochoa, Ruben O.
    Leclair, Alexandre
    Wang, Qian
    Zh, Jieping
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (40) : 9477 - 9484
  • [14] Erythrosine B Catalyzed Synthesis of trans-Dihydro-4H-furo[3,2-c]- chromen-4-ones through Photocatalytic Dehydrogenative sp3 C-O Bond Formation
    Das, Sourav
    Paul, Suvam
    Choudhuri, Tathagata
    Sikdar, Papiya
    Bagdi, Avik Kumar
    SYNTHESIS-STUTTGART, 2023, 55 (13): : 2027 - 2036
  • [15] Diastereoselective sp3 C-O Bond Formation via Visible Light-Induced, Copper-Catalyzed Cross-Couplings of Glycosyl Bromides with Aliphatic Alcohols
    Yu, Fei
    Dickson, Jalen L.
    Loka, Ravi S.
    Xu, Hengfu
    Schaugaard, Richard N.
    Schlegel, H. Bernhard
    Luo, Long
    Nguyen, Hien M.
    ACS CATALYSIS, 2020, 10 (11) : 5990 - 6001
  • [16] A Ni3V2O8@g-CN nanocomposite-based p-n heterojunction: mechanistic insights into photocatalytic activation of the inert C(sp3)-H bond
    Verma, Anjali
    Jaryal, Arpna
    Chauhan, Deepak Kumar
    Battula, Venugopala Rao
    Sarkar, Madhurima
    Patra, Abhijit
    Kailasam, Kamalakannan
    SUSTAINABLE ENERGY & FUELS, 2023, 7 (11) : 2727 - 2739