Photosubstitution of Dicyanoarenes by Hypervalent Allylsilicon Reagents via Photoinduced Electron Transfer

被引：31
|
作者：
Matsuoka, Daisuke [1 ]
Nishigaichi, Yutaka [1 ]
机构：
[1] Shimane Univ, Grad Sch Sci & Engn, Dept Mat Sci, Matsue, Shimane 6908504, Japan
来源：
CHEMISTRY LETTERS | 2014年 / 43卷 / 04期
关键词：
TRANSFER-INITIATED PHOTOADDITION; PHOTOCHEMICAL-REACTIONS; ALLYLIC SILANES; CATION; DICYANOBENZENES; PHOTOALLYLATION; DESILYLATION; ALLYLATION;
D O I：
10.1246/cl.131132
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Photosubstitution of dicyanoarenes with hypervalent allylsilicon reagents in the presence of anthracene efficiently proceeded to afford the allyl-substituted product in moderate to good yields. The efficiency for the present photoreaction was much higher than that for the tetracoordinate allylsilanes, because hypervalent allylsilicon reagents possess lower oxidation potential than the tetracoordinate ones, which resulted in more efficient photoinduced electron-transfer process.
引用
收藏
页码：559 / 561
页数：3
相关论文
共 50 条
  • [1] First examples of hypervalent enhancement of photoallylation by allylsilicon compounds via photoinduced electron transfer
    Nishigaichi, Y
    Suzuki, A
    Saito, T
    Takuwa, A
    TETRAHEDRON LETTERS, 2005, 46 (31) : 5149 - 5151
  • [2] Photoinduced electron transfer from isoprenoid polyalkene acetates to dicyanoarenes
    Warzecha, KD
    Gorner, H
    Demuth, M
    JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1998, 94 (12): : 1701 - 1706
  • [3] PHOTOSUBSTITUTION OF DICYANOBENZENES BY ALLYLIC SILANES, GERMANES, AND STANNANES VIA PHOTOINDUCED ELECTRON-TRANSFER
    NAKANISHI, K
    MIZUNO, K
    OTSUJI, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (08) : 2371 - 2379
  • [4] PHOTOSUBSTITUTION OF DICYANOBENZENES BY GROUP-14 ORGANOMETALLIC COMPOUNDS VIA PHOTOINDUCED ELECTRON-TRANSFER - ADDITIVE AND MEDIUM EFFECTS ON PHOTOINDUCED ELECTRON-TRANSFER REACTION
    MIZUNO, K
    NAKANISHI, K
    OTSUJI, Y
    CHEMISTRY LETTERS, 1988, (11) : 1833 - 1836
  • [5] Fluorescent PET (photoinduced electron transfer) reagents for thiols
    de Silva, AP
    Gunaratne, HQN
    Gunnlaugsson, T
    TETRAHEDRON LETTERS, 1998, 39 (28) : 5077 - 5080
  • [6] Allyl-transfer Reaction from Photoexcited Hypervalent Allylsilicon Reagent toward Dicyanobenzenes
    Matsuoka, Daisuke
    Nishigaichi, Yutaka
    CHEMISTRY LETTERS, 2015, 44 (02) : 163 - 165
  • [7] Cycloreversion of β-lactams via photoinduced electron transfer
    Perez-Ruiz, Raul
    Saez, Jose A.
    Consuelo Jimenez, M.
    Miranda, Miguel A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (42) : 8428 - 8432
  • [8] Photooxygenation of Aryldisilanes via Photoinduced Electron Transfer
    Mizuno, K.
    Tamai, T.
    Hashida, I.
    Otsuji, Y.
    Journal of Information Technology, 10 (01):
  • [9] Redox catalysis via photoinduced electron transfer
    Lee, Yong-Min
    Nam, Wonwoo
    Fukuzumi, Shunichi
    CHEMICAL SCIENCE, 2023, 14 (16) : 4205 - 4218
  • [10] The influence of changes in the dipole moment of reagents on the rate of photoinduced electron transfer
    Khokhlova, S. S.
    Mikhailova, V. A.
    Ivanov, A. I.
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 82 (06) : 1024 - 1030
12345