Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides

被引：47
|
作者：
Couty, S [1 ]
Barbazanges, M [1 ]
Meyer, C [1 ]
Cossy, J [1 ]
机构：
[1] Ecole Super Phys & Chim Ind Ville Paris, Assoc CNRS, Chim Organ Lab, F-75231 Paris, France
来源：
SYNLETT | 2005年 / 06期
关键词：
cross-coupling; palladium; enamides; eliminations; ynamides;
D O I：
10.1055/s-2005-864821
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
beta,beta-Dihaloenamides can be successfully involved in palladium-catalyzed Suzuki-Miyaura coupling reactions. Whereas the resulting trisubstituted (Z)-beta-bromoenamides could participate in a second cross-coupling leading to beta, beta-disubstituted enamides, the (Z)-beta-chloroenamides have been converted to disubstituted ynamides by an E-2 elimination.
引用
收藏
页码：905 / 910
页数：6
相关论文
共 50 条
  • [31] Efficient Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Iodoethynes with Arylboronic Acids under Aerobic Conditions
    Tang, Jian-Sheng
    Xie, Ye-Xiang
    Wang, Zhi-Qiang
    Li, Jin-Heng
    SYNTHESIS-STUTTGART, 2011, (17): : 2789 - 2795
  • [32] Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation
    Wang, Zi
    Orellana, Arturo
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (47) : 11445 - 11449
  • [33] Palladium-catalyzed Suzuki-Miyaura cross-coupling using phosphinous acids and dialkyl(chloro)phosphane ligands
    Wolf, C
    Ekoue-Kovi, K
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (08) : 1917 - 1925
  • [34] Palladium-catalyzed Suzuki-Miyaura reaction involving a secondary sp3 carbon:: Studies of stereochemistry and scope of the reaction
    Rodriguez, Nuria
    Ramirez de Arellano, Carmen
    Asensio, Gregorio
    Medio-Simon, Mercedes
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (15) : 4223 - 4229
  • [35] Suzuki-Miyaura Coupling Reactions of Fluorohalobenzenes
    Iqbal, Shoaib
    Sharif, Muhammad
    Langer, Peter
    SYNLETT, 2021, 32 (18) : 1784 - 1795
  • [36] Caffeine and theophylline as sustainable, biosourced NHC ligand precursors for efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reactions
    Mazars, Francois
    Zaragoza, Guillermo
    Delaude, Lionel
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2022, 978
  • [37] Density functional studies on palladium-catalyzed Suzuki-Miyaura cross-coupling reactions assisted by N- or P-chelating ligands
    Huang, Yi-Luen
    Weng, Chia-Ming
    Hong, Fung-E.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (14) : 4426 - 4434
  • [38] One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki-Miyaura Cross-Coupling
    Baumgartner, Yann
    Baudoin, Olivier
    ACS CATALYSIS, 2020, 10 (18) : 10508 - 10515
  • [39] Palladium-catalyzed Suzuki-Miyaura reaction of fluorinated vinyl chloride: a new approach for synthesis α and α,β-trifluoromethylstyrenes
    Li, Yang
    Zhao, Bo
    Dai, Kun
    Tu, Dong-Huai
    Wang, Bo
    Wang, Yao-Yu
    Liu, Zhao-Tie
    Liu, Zhong-Wen
    Lu, Jian
    TETRAHEDRON, 2016, 72 (37) : 5684 - 5690
  • [40] Synthesis of biphenylamines via Suzuki-Miyaura cross-coupling reactions
    Maj, Anna M.
    Delaude, Lionel
    Demonceau, Albert
    Noels, Alfred F.
    TETRAHEDRON, 2007, 63 (12) : 2657 - 2663
12345