Photoinduced addition and addition-elimination reactions of perfluoroalkyl iodides to electron-deficient olefins

被引：38
|
作者：
Yajima, Tomoko [1 ]
Jahan, Ishrat [1 ]
Tonoi, Takayuki [1 ]
Shinmen, Manami [1 ]
Nishikawa, Aya [1 ]
Yamaguchi, Kanako [1 ]
Sekine, Izumi [1 ]
Nagano, Hajime [1 ]
机构：
[1] Ochanomizu Univ, Dept Chem, Bunkyo Ku, Otsuka, Tokyo 1128610, Japan
来源：
TETRAHEDRON | 2012年 / 68卷 / 34期
关键词：
Iodoperfluoroalkylation; Addition-elimination reaction; Electron-deficient olefin; Photoinduced radical reaction; SILYL ENOL ETHERS;
D O I：
10.1016/j.tet.2012.06.028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Photoinduced radical perfluoroalkylation of various simple electron-deficient olefins was achieved in the presence of an aqueous Na2S2O3 solution. The reactions proceeded smoothly to give addition or addition elimination products. The ability of the products to be used as radical precursors or Michael acceptors was also demonstrated. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6856 / 6861
页数：6
相关论文
共 50 条
  • [1] REACTION OF PERFLUOROALKYL IODIDES WITH ELECTRON-DEFICIENT OLEFINS UNDER UV IRRADIATION
    QIU, ZM
    BURTON, DJ
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3465 - 3472
  • [2] Reaction of perfluoroalkyl iodides with electron-deficient olefins under UV irradiation
    J Org Chem, 11 (3465):
  • [3] Hydroperfluoroalkylation of electron-deficient olefins with perfluoroalkyl iodides promoted by zinc/viologen
    Zhou, Sheng-Hua
    Lin, Jin-Hong
    Zhao, Gang
    Xiao, Ji-Chang
    Cao, Wei-Guo
    RSC ADVANCES, 2016, 6 (65): : 60080 - 60083
  • [4] ADDITION OF PERFLUOROALKYL IODIDES TO OLEFINS INITIATED BY ELECTRON-TRANSFER
    FEIRING, AE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 18 - FLO
  • [5] ADDITION-ELIMINATION REACTION IN THE TRIFLUOROACETYLATION OF ELECTRON-RICH OLEFINS
    MORIGUCHI, T
    ENDO, T
    TAKATA, T
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3523 - 3528
  • [6] REACTION OF PERFLUOROALKYL IODIDES WITH ELECTRON-DONOR NUCLEOPHILES - ADDITION OF PERFLUOROALKYL IODIDES TO OLEFINS INITIATED BY ELECTRON-TRANSFER
    FEIRING, AE
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18): : 3269 - 3274
  • [7] Borohydride-Mediated Radical Addition Reactions of Organic Iodides to Electron-Deficient Alkenes
    Kawamoto, Takuji
    Uehara, Shohei
    Hirao, Hidefumi
    Fukuyama, Takahide
    Matsubara, Hiroshi
    Ryu, Ilhyong
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 3999 - 4007
  • [8] Rongalite-initiated addition of perfluoroalkyl iodides to olefins
    HUANG
    LIU
    Chinese Journal of Chemistry, 1990, (04) : 358 - 361
  • [9] STUDY OF PHOTOCHEMICAL ADDITION OF ACYL RADICAL TO ELECTRON-DEFICIENT OLEFINS
    MACIAS, FA
    MOLINILLO, JMG
    MASSANET, GM
    RODRIGUEZLUIS, F
    TETRAHEDRON, 1992, 48 (16) : 3345 - 3352
  • [10] UV INITIATED ADDITION OF IODODIFLUOROMETHYL KETONES TO ELECTRON-DEFICIENT OLEFINS
    QIU, ZM
    BURTON, DJ
    TETRAHEDRON LETTERS, 1994, 35 (12) : 1813 - 1816
12345