Palladium-Catalyzed Dehydrogenative Coupling of Furans with Styrenes

被引：65
作者：
Aouf, Chahinez [1 ]
Thiery, Emilie [1 ]
Le Bras, Jean [1 ]
Muzart, Jacques [1 ]
机构：
[1] Univ Reims, Inst Chim Mol Reims, CNRS, UMR 6229,UFR Sci Exactes & Nat, F-51687 Reims 2, France
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 18期
关键词：
C-H ALKENYLATION; FREE NH-INDOLES; BOND FUNCTIONALIZATION; MOLECULAR-OXYGEN; OLEFINS; ARENES; ACTIVATION; OXIDANT; C3-ALKENYLATION; THIOPHENES;
D O I：
10.1021/ol901570p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Under palladium(II)-catalyzed and oxidative conditions, the coupling of furans with styrenes leads to the formation of Heck-type products in medium to good yields. The reaction is highly regio- and stereoselective, giving trans-olefins predominantly.
引用
收藏
页码：4096 / 4099
页数：4
相关论文
共 35 条
  • [1] Electrochemical recycling of benzoquinone in the Pd/benzoquinone-catalyzed Heck-type reactions from arenes
    Amatore, Christian
    Cammoun, Chama
    Jutand, Anny
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) : 292 - 296
  • [2] Structures, spectra and photophysics of new organic fluorophores: 2,3-and 2,5-di(phenylethenyl)furan
    Baraldi, Ivan
    Benassi, Enrico
    Ciorba, Serena
    Sindler-Kulyk, Marija
    Skoric, Irena
    Spalletti, Anna
    [J]. CHEMICAL PHYSICS, 2008, 353 (1-3) : 163 - 169
  • [3] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [4] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles
    Beck, EM
    Grimster, NP
    Hatley, R
    Gaunt, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2528 - 2529
  • [5] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
    Boele, MDK
    van Strijdonck, GPF
    de Vries, AHM
    Kamer, PCJ
    de Vries, JG
    van Leeuwen, PWNM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) : 1586 - 1587
  • [6] Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions
    Cai, Guixin
    Fu, Ye
    Li, Yizhou
    Wan, Xiaobing
    Shi, Zhangjie
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) : 7666 - 7673
  • [7] Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles
    Capito, E
    Brown, JM
    Ricci, A
    [J]. CHEMICAL COMMUNICATIONS, 2005, (14) : 1854 - 1856
  • [8] Direct and Regioselective C-H Alkenylation of Tetrahydropyrido[1,2-a]pyrimidines
    Cheng, Dachen
    Gallagher, Timothy
    [J]. ORGANIC LETTERS, 2009, 11 (12) : 2639 - 2641
  • [9] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes
    Cho, Seung Hwan
    Hwang, Seung Jun
    Chang, Sukbok
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9254 - +
  • [10] Recent progress in Wacker oxidations: Moving toward molecular oxygen as the sole oxidant
    Cornell, Candace N.
    Sigman, Matthew S.
    [J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1903 - 1909
1234