Ruthenium-Catalyzed Heck-Type Alkenylation of Alkyl Bromides

被引：6
|
作者：
Maria Munoz-Molina, Jose [1 ]
Perez, Pedro J. [1 ]
机构：
[1] Univ Huelva, Lab Catalisis Homogenea, CIQSO Ctr Invest Quim Sostenible, Unidad Asociada,CSIC, Huelva 21007, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 12期
关键词：
TRANSFER RADICAL-ADDITION; ELECTRON-DEFICIENT; COUPLING REACTIONS; EFFICIENT; ALKENES; HALIDES; BENZYL; DIFLUOROALKYLATION; SECONDARY; LIGHT;
D O I：
10.1021/acs.joc.9b00898
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The complex [Cp*RuCl(PPh3)(2)] displays a high catalytic activity for the Heck-type alkenylation of alkyl bromides in the first example using this metal under thermal conditions. The coupling reaction proceeds efficiently with a variety of functionalized tertiary, secondary, and primary alkyl bromides. The presence of Hunig's base has been revealed to be crucial for this transformation. Preliminary mechanistic studies support the participation of alkyl radicals in the reaction.
引用
收藏
页码：8289 / 8296
页数：8
相关论文
共 50 条
  • [1] Iron-Catalyzed Heck-Type Alkenylation of Functionalized Alkyl Bromides
    Zhu, Kailong
    Dunne, Joanne
    Shaver, Michael P.
    Thomas, Stephen P.
    ACS CATALYSIS, 2017, 7 (04): : 2353 - 2356
  • [2] Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary a-Carbonyl Alkyl Bromides
    Liu, Chao
    Tang, Shan
    Liu, Dong
    Yuan, Jiwen
    Zheng, Liwei
    Meng, Lingkui
    Lei, Aiwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (15) : 3638 - 3641
  • [3] Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides
    Fan, Tao
    Meng, Wei-Dong
    Zhang, Xingang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2610 - 2616
  • [4] Ruthenium-catalyzed Heck-type olefination and Suzuki coupling reactions: Studies on the nature of catalytic species
    Na, Y
    Park, S
    Han, SB
    Han, H
    Ko, S
    Chang, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) : 250 - 258
  • [5] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    McMahen, Rebecca L.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) : 20146 - 20148
  • [6] Transition-Metal-Catalyzed Alkyl Heck-Type Reactions
    Kurandina, Daria
    Chuentragool, Padon
    Gevorgyan, Vladimir
    SYNTHESIS-STUTTGART, 2019, 51 (05): : 985 - 1005
  • [7] Palladium-Catalyzed Heck-Type Difluoroalkylation of Alkenes with Functionalized Difluoromethyl Bromides
    Zhang, Feng
    Min, Qiao-Qiao
    Zhang, Xingang
    SYNTHESIS-STUTTGART, 2015, 47 (19): : 2912 - 2923
  • [8] Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12823 - 12825
  • [9] Palladium-catalyzed intermolecular Heck-type reactions with alkyl iodides
    McMahon, Caitlin
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [10] Ruthenium-catalyzed oxidative Heck reactions
    Farrington, EJ
    Brown, JM
    Barnard, CFJ
    Rowsell, E
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (01) : 169 - 171
12345