Visible-Light-Induced Regioselective C(sp3)-H Acyloxylation of Aryl-2H-azirines with (Diacetoxy)iodobenzene

被引：41
作者：
De, Aramita [1 ]
Santra, Sougata [2 ]
Hajra, Alakananda [1 ]
Zyryanov, Grigory V. [2 ,3 ]
Majee, Adinath [1 ]
机构：
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
[2] Ural Fed Univ, Chem Engn Inst, Dept Organ & Biomol Chem, 19 Mira St, Ekaterinburg 620002, Russia
[3] Russian Acad Sci, Ural Div, I Ya Postovskiy Inst Organ Synth, 22 Sofi Kovalevskoy St, Ekaterinburg 620219, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期
基金：
俄罗斯科学基金会;
关键词：
SYNTHETIC APPLICATIONS; PHOTOREDOX CATALYSIS; VINYL AZIDES; OXIDATION; 2H-AZIRINES; FUNCTIONALIZATION; DERIVATIVES; CYCLIZATION; ACTIVATION; ALKYNES;
D O I：
10.1021/acs.joc.9b01625
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible-light-promoted regioselective coupling of C(sp(3))-H of aryl-2H-azirine and (diacetoxy)-iodobenzene has been reported. Rose Bengal as an organo-photoredox catalyst has been used in this reaction. The reaction proceeds under aerobic condition at room temperature. A variety of aryl-2H-azirines gives the corresponding acyloxylated azirines under this reaction conditions. The reaction goes through a radical pathway. The protocol is also applicable on gram-scale synthesis.
引用
收藏
页码：11735 / 11740
页数：6
相关论文
共 63 条
  • [1] Transition-Metal-Catalyzed Synthesis of Hydroxylated Arenes
    Alonso, Diego A.
    Najera, Carmen
    Pastor, Isidro M.
    Yus, Miguel
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) : 5274 - 5284
  • [2] [3+2]-Cycloaddition of 2H-Azirines with Nitrosoarenes: Visible-Light-Promoted Synthesis of 2,5-Dihydro-1,2,4-oxadiazoles
    Cai, Bao-Gui
    Chen, Ze-Le
    Xu, Guo-Yong
    Xuan, Jun
    Xiao, Wen-Jing
    [J]. ORGANIC LETTERS, 2019, 21 (11) : 4234 - 4238
  • [3] Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions
    Chatterjee, Rana
    Samanta, Satyajit
    Mukherjee, Anindita
    Santra, Sougata
    Zyryanov, Grigory V.
    Majee, Adinath
    [J]. TETRAHEDRON LETTERS, 2019, 60 (03) : 276 - 283
  • [4] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers
    Chen, Fa-Jie
    Zhao, Sheng
    Hu, Fang
    Chen, Kai
    Zhang, Qi
    Zhang, Shuo-Qing
    Shi, Bing-Feng
    [J]. CHEMICAL SCIENCE, 2013, 4 (11) : 4187 - 4192
  • [5] Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton
    Chen, Lili
    Li, Hongji
    Li, Pinhua
    Wang, Lei
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3646 - 3649
  • [6] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
    Chen, Mark S.
    White, M. Christina
    [J]. SCIENCE, 2007, 318 (5851) : 783 - 787
  • [7] Asymmetric synthesis of 2H-Azirine 2-carboxylate esters
    Davis, FA
    Liu, H
    Liang, CH
    Reddy, GV
    Zhang, YL
    Fang, TN
    Titus, DD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) : 8929 - 8935
  • [8] SILVER ION INDUCED REACTIONS OF ALPHA-HALOIMINES
    DEKIMPE, N
    STEVENS, C
    [J]. TETRAHEDRON, 1990, 46 (19) : 6753 - 6770
  • [9] DEKIMPE N, 1982, TETRAHEDRON LETT, V23, P2853
  • [10] 1,3-Diamine Formation from an Interrupted Hofmann-Loffler Reaction: Iodine Catalyst Turnover through Ritter-Type Amination
    Duhamel, Thomas
    Martinez, Mario D.
    Sideri, Ioanna K.
    Muniz, Kilian
    [J]. ACS CATALYSIS, 2019, 9 (09): : 7741 - 7745
1234567