Novel three-component reactions based on a Heck carbopalladation/cyclization domino reaction

被引:38
|
作者
Kressierer, CJ [1 ]
Müller, TJJ [1 ]
机构
[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
amination; C-C coupling; domino reactions; multicomponent reactions; olefination;
D O I
10.1002/anie.200461134
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In one fell swoop: the reaction of alkynyl-allyl alcohols with aryl halides in the presence of [Pd(PPh3)2Cl2] under Heck reaction conditions provides cyclic γ,δ-enals (see scheme). This reaction serves as the starting sequence for the one-pot synthesis of diene esters and β-amino-substituted tetrahydrofurans.
引用
收藏
页码:5997 / 6000
页数:4
相关论文
共 50 条
  • [1] Three-component coupling of benzyne: Domino intermolecular carbopalladation
    Henderson, Jaclyn L.
    Edwards, Andrew S.
    Greaney, Michael F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) : 7426 - 7427
  • [2] Three-component cascade carbopalladation/Heck cyclization/borylation: facile access to boryl-functionalized indenes
    Sun, Fei
    Zheng, Yiyi
    Wu, Mingxia
    Ji, Hongsen
    Jiang, Zhongyao
    Liu, Chenglin
    Wu, Xin-Xing
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (62) : 8075 - 8078
  • [3] Three-Component (Domino) Reaction Affording Substituted Pyrroloquinazolines: Cyclization Regioselectivity and Stereoselectivity
    Paleta, Oldrich
    Dolensky, Bohumil
    Palecek, Jiri
    Kvicala, Jaroslav
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (07) : 1262 - 1270
  • [4] Nucleophilic trapping of π-allylpalladium intermediates generated by carbopalladation of bicyclopropylidene:: A novel three-component reaction
    Nüske, H
    Noltemeyer, M
    de Meijere, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (18) : 3411 - +
  • [5] Sequential three-component and Heck reactions for the synthesis of phenanthridones
    Jacobi von Wangelin, A
    Neumann, H
    Gördes, D
    Hübner, S
    Wendler, C
    Klaus, S
    Strübing, D
    Spannenberg, A
    Jiao, HJ
    El Firdoussi, L
    Thurow, K
    Stoll, N
    Beller, M
    [J]. SYNTHESIS-STUTTGART, 2005, (12): : 2029 - 2038
  • [6] A novel atom-economic synthesis of functionalized imidazolidines through copper(I)-catalyzed domino three-component coupling and cyclization reactions
    Li, Yufeng
    Wu, Zhengguang
    Shi, Jie
    Bu, Hongzhong
    Gu, Jiachao
    Pan, Yi
    [J]. TETRAHEDRON, 2014, 70 (19) : 3134 - 3140
  • [7] Catalytic Three-Component Domino Reaction for the Preparation of Trisubstituted Oxazoles
    v Wachenfeldt, Henrik
    Roese, Philipp
    Paulsen, Filip
    Loganathan, Nagarajan
    Strand, Daniel
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (24) : 7982 - 7988
  • [8] A One-Pot, Three-Component Approach to Functionalised Tetrahydroisoquinolines Using Domino Heck-aza-Michael Reactions
    Priebbenow, Daniel L.
    Pfeffer, Frederick M.
    Stewart, Scott G.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1632 - 1635
  • [9] Highly Regioselective Three-Component Domino Heck-Negishi Coupling Reaction for the Functionalization of Purines at C6
    Wang, Dong-Chao
    Niu, Hong-Ying
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Wang, Hui-Xuan
    Guo, Hai-Ming
    [J]. ORGANIC LETTERS, 2014, 16 (01) : 262 - 265
  • [10] One-pot synthesis of novel functionalized benzodiazepines via three-component or domino reactions
    Sun, Yue-Wei
    Wang, Lan-Zhi
    [J]. NEW JOURNAL OF CHEMISTRY, 2018, 42 (24) : 20032 - 20040