Palladium-catalyzed regiocontrolled internal heteroarylation of electron-rich olefins with heteroaryl halides

被引：12
|
作者：
Xu, Dan [1 ]
Liu, Zhihua [1 ]
Tang, Weijun [1 ]
Xu, Lijin [1 ]
Hyder, Zeynab [2 ]
Xiao, Jianliang [2 ]
机构：
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
[2] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 42期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/j.tetlet.2008.08.005
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient palladium-catalyzed Heck coupling reaction of heteroaryl halides with electron-rich vinyl ether and hydroxyalkyl vinyl ethers is described. It was found that the choice of solvent, ligand, and reaction temperature had a fundamental influence on the regioselectivity and reactivity of the reaction, and the combination of Pd(OAc)(2) and DPPF in ethylene glycol led to the most effective catalytic system. Under these conditions, a variety of heteroaryl halides reacted very quickly with electron-rich olefins to afford exclusively the branched products in good to excellent yields without employing triflates, halide scavengers, or ionic liquids. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6104 / 6107
页数：4
相关论文
共 50 条
  • [21] Palladium-catalyzed arylation and heteroarylation of azolopyrimidines
    Mendiola, J
    Castellote, I
    Alvarez-Builla, J
    Fernández-Gadea, J
    Gómez, A
    Vaquero, JJ
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03): : 1254 - 1257
  • [22] Palladium-catalyzed aminoallylation of activated olefins with allylic halides and phthalimide
    Aoyagi, K
    Nakamura, H
    Yamamoto, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17): : 5977 - 5980
  • [23] Palladium-catalyzed highly regioselective and stereoselective arylation of electron-rich allylamines with aryl bromides
    Jiang, Zhen
    Zhang, Lingjuan
    Dong, Chaonan
    Ma, Baode
    Tang, Weijun
    Xu, Lijin
    Fan, Qinghua
    Xiao, Jianliang
    TETRAHEDRON, 2012, 68 (24) : 4919 - 4926
  • [24] Palladium-catalyzed heteroannulation of internal alkynes by vinylic halides
    Larock, RC
    Doty, MJ
    Han, XJ
    TETRAHEDRON LETTERS, 1998, 39 (29) : 5143 - 5146
  • [25] Palladium-Catalyzed Hydroxylation of Aryl and Heteroaryl Halides Enabled by the Use of a Palladacycle Precatalyst
    Cheung, Chi Wai
    Buchwald, Stephen L.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (11): : 5351 - 5358
  • [26] Palladium-catalyzed aminocarbonylation of heteroaryl halides using di-tert-butylphosphinoferrocene
    Qu, Bo
    Haddad, Nizar
    Han, Zhengxu S.
    Rodriguez, Sonia
    Lorenz, Jon C.
    Grinberg, Nelu
    Lee, Heewon
    Busacca, Carl A.
    Krishnamurthy, DhileepKumar
    Senanayake, Chris H.
    TETRAHEDRON LETTERS, 2009, 50 (45) : 6126 - 6129
  • [27] Photoinduced Palladium-Catalyzed 1,2-Difunctionalization of Electron-Rich Olefins via a Reductive Radical-Polar Crossover Reaction
    Fang, Hao
    Empel, Claire
    Atodiresei, Iuliana
    Koenigs, Rene M.
    ACS CATALYSIS, 2023, 13 (09) : 6445 - 6451
  • [28] Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides
    Shavnya, Andrei
    Coffey, Steven B.
    Smith, Aaron C.
    Mascitti, Vincent
    ORGANIC LETTERS, 2013, 15 (24) : 6226 - 6229
  • [29] Palladium-catalyzed direct heteroarylation of chloropyridines and chloroquinolines
    Derridj, Fazia
    Roger, Julien
    Geneste, Florence
    Djebbar, Safia
    Doucet, Henri
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (03) : 455 - 465
  • [30] REACTIVITY OF ELECTRON-RICH OLEFINS .7. SYNTHESIS OF PHENOLALDEHYDES WITH ELECTRON-RICH OLEFINS
    HOCKER, J
    GIESECKE, H
    MERTEN, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (03): : 169 - 170
12345