FeCl2-Catalyzed selective C-C bond formation by oxidative activation of a benzylic C-H bond

被引:335
作者
Li, Zhiping [1 ]
Cao, Lin
Li, Chao-Jun
机构
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
[2] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
C-H activation; cross-coupling; iron; peroxides redox; chemistry;
D O I
10.1002/anie.200701782
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Any old iron: Readily available and non-toxic FeCl2 effectively catalyzes C-C bond formation by oxidative activation of benzylic C-H bonds in the presence of tert-butyl peroxide as a stoichiometric oxidant (see scheme). The mild reaction conditions, good yields, low catalyst cost, and easy operation are the major advantages of this cross-dehydrogenation coupling reaction. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6505 / 6507
页数:3
相关论文
共 27 条
  • [1] [Anonymous], 2005, ANGEW CHEM
  • [2] PtBr2-catalyzed transformation of allyl(o-ethynylaryl)carbinol derivatives into functionalized indenes.: Formal sp3 C-H bond activation
    Bajracharya, Gan B.
    Pahadi, Nirmal K.
    Gridnev, Ilya D.
    Yamamoto, Yoshinori
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) : 6204 - 6210
  • [3] Baran P.S., 2006, ANGEW CHEM, V118, P7241
  • [4] Oxidative C-C bond formation in heterocyclic chemistry
    Baran, Phil S.
    Ambhaikar, Narendra B.
    Guerrero, Carlos A.
    Hafensteiner, Benjamin D.
    Lin, David W.
    Richter, Jeremy M.
    [J]. ARKIVOC, 2006, : 310 - 325
  • [5] Intermolecular oxidative enolate heterocoupling
    Baran, Phil S.
    DeMartino, Michael P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) : 7083 - 7086
  • [6] THE SELECTIVE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS - GIF CHEMISTRY
    BARTON, DHR
    DOLLER, D
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (11) : 504 - 512
  • [7] An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides
    Bica, K
    Gaertner, P
    [J]. ORGANIC LETTERS, 2006, 8 (04) : 733 - 735
  • [8] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254
  • [9] Asymmetric intermolecular C-H functionalization of benzyl silyl ethers mediated by chiral auxiliary-based aryldiazoacetates and chiral dirhodium catalysts
    Davies, HML
    Hedley, SJ
    Bohall, BR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) : 10737 - 10742
  • [10] Catalytic asymmetric benzylic C-H activation by means of carbenoid-induced C-H insertions
    Davies, HML
    Jin, QH
    Ren, PD
    Kovalevsky, AY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) : 4165 - 4169