Ligand-Free Copper-Catalyzed Arylation of Olefins by the Mizoroki-Heck Reaction

被引：26
|
作者：
Peng, Yong [1 ]
Chen, Jiuxi [1 ]
Ding, Jinchang [1 ,2 ]
Liu, Miaochang [1 ]
Gao, Wenxia [1 ]
Wu, Huayue [1 ]
机构：
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Wenzhou Vocat & Tech Coll, Wenzhou 325035, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2011年 / 02期
基金：
中国国家自然科学基金;
关键词：
ligand-free; copper-catalyzed; Mizoroki-Heck reaction; cross-coupling; E-internal olefins; COUPLING REACTIONS; ARYL; EFFICIENT; COMPLEXES; BROMIDES; ALKENES; HALIDES; PEG; CO;
D O I：
10.1055/s-0030-1258338
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel ligand-free copper-catalyzed Mizoroki-Heck cross-coupling reaction of various aryl iodides with olefins has been developed. Both the solvent and the base were found to have a fundamental influence on the efficiency of the transformation in the presence of 10 mol% Cu2O, with DMF and tetramethylammonium bromide (TMAB) being the optimal solvent and base, respectively. As a result, a set of the corresponding E-internal olefins were obtained selectively in moderate to good yields.
引用
收藏
页码：213 / 216
页数：4
相关论文
共 50 条
  • [1] Synthesis of α-Trifluoromethylacrylates by Ligand-Free Palladium-Catalyzed Mizoroki-Heck Reaction
    Xiao, Pan
    Schlinquer, Claire
    Pannecoucke, Xavier
    Bouillon, Jean-Philippe
    Couve-Bonnaire, Samuel
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 2072 - 2082
  • [2] Ligand-free palladium-catalyzed Mizoroki-Heck reaction to synthesize valuable α-trifluoromethylacrylates
    Xiao, Pan
    Schlinquer, Claire
    Pannecoucke, Xavier
    Couve-Bonnaire, Samuel
    Bouillon, Jean-Philippe
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2020, 233
  • [3] Ligand-Free Copper-Catalyzed Arylation of Amidines
    Cortes-Salva, Michelle
    Garvin, Corey
    Antilla, Jon C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05): : 1456 - 1459
  • [4] A novel hydrophobic fluorous ionic liquid for ligand-free Mizoroki-Heck reaction
    Gaikwad, Dipak S.
    Park, YoonKook
    Pore, Dattaprasad M.
    [J]. TETRAHEDRON LETTERS, 2012, 53 (24) : 3077 - 3081
  • [5] Double Mizoroki-Heck Arylation of Terminal Alkenes in the Presence of "Ligand-Free" Palladium Catalytic Systems
    Kurokhtina, A. A.
    Larina, E. V.
    Lagoda, N. A.
    Grigoryeva, T. A.
    Schmidt, A. F.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (10) : 1704 - 1708
  • [6] Ligand-free ultrasmall palladium nanoparticle catalysis for the Mizoroki-Heck reaction in aqueous micelles
    Luo, Xiaojun
    Wu, Siyuan
    Hou, Linxi
    Ge, Xin
    [J]. NEW JOURNAL OF CHEMISTRY, 2024, 48 (16) : 7102 - 7110
  • [7] Ligand-free copper-catalyzed denitrogenative arylation of phosphorylamides with arylhydrazines
    Zhu, Qiao
    Che, Shiying
    Luo, Zhenghong
    Zhao, Zijian
    [J]. SYNTHETIC COMMUNICATIONS, 2020, 50 (07) : 947 - 957
  • [8] Efficient Ligand-Free Copper-Catalyzed Arylation of Aliphatic Amines
    Yong, Fui-Fong
    Teo, Yong-Chua
    [J]. SYNLETT, 2010, (20) : 3068 - 3072
  • [9] Phosphine-free palladium catalyzed Mizoroki-Heck reaction using hydrazone as a ligand
    Mino, Takashi
    Shirae, Yoshiaki
    Sasai, Yousuke
    Sakamoto, Masami
    Fujita, Tsutomu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18): : 6834 - 6839
  • [10] Ligand-free copper-catalyzed O-arylation of nitroarenes with phenols
    Chen, Jiuxi
    Wang, Xingyong
    Zheng, Xingwang
    Ding, Jinchang
    Liu, Miaochang
    Wu, Huayue
    [J]. TETRAHEDRON, 2012, 68 (43) : 8905 - 8907
12345