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
  • [31] Ruthenium-Catalyzed α-Regioselective Hydroboration of Allenes
    Tan, Yun-Xuan
    Li, Shijia
    Chen, Liang
    Huang, Jing
    Zhang, Chaoshen
    Song, Lijuan
    Zhang, Xinhao
    Wu, Yun-Dong
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (08)
  • [32] Manganese-Catalyzed Alkyl-Heck-Type Reaction via Oxidative Decarbonylation of Aldehydes
    Zong, Zhenzhen
    Wang, Wenxiao
    Bai, Xiaohui
    Xi, Hui
    Li, Zhiping
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (07) : 622 - 625
  • [33] Palladium-catalysed Heck-type alkenylation reactions in the synthesis of quinolines. Mechanistic insights and recent applications
    Carral-Menoyo, Asier
    Sotomayor, Nuria
    Lete, Esther
    CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (16) : 5345 - 5361
  • [34] Expeditious enyne construction from alkynes via oxidative Pd(II)-catalyzed Heck-type coupling
    Hadi, Victor
    Yoo, Kyung Soo
    Jeong, Min
    Jung, Kyung Woon
    TETRAHEDRON LETTERS, 2009, 50 (20) : 2370 - 2373
  • [35] A transition-metal-free Heck-type reaction between alkenes and alkyl iodides enabled by light in water
    Liu, Wenbo
    Li, Lu
    Chen, Zhengwang
    Li, Chao-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (22) : 6170 - 6174
  • [36] Ruthenium-catalyzed direct oxidative alkenylation of arenes through twofold C-H bond functionalization
    Kozhushkov, Sergei I.
    Ackermann, Lutz
    CHEMICAL SCIENCE, 2013, 4 (03) : 886 - 896
  • [37] Cobalt(I)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides
    Verma, Piyush Kumar
    Prasad, K. Sujit
    Varghese, Dominic
    Geetharani, K.
    ORGANIC LETTERS, 2020, 22 (04) : 1431 - 1436
  • [38] Palladium-catalyzed intermolecular Heck reaction of alkyl halides
    Zou, Yinjun
    Zhou, Jianrong
    CHEMICAL COMMUNICATIONS, 2014, 50 (28) : 3725 - 3728
  • [39] Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes
    Zhou, Lu
    Zhu, Chuan
    Bi, Peijia
    Feng, Chao
    CHEMICAL SCIENCE, 2019, 10 (04) : 1144 - 1149
  • [40] Bench-Stable Nickel Precatalysts with Heck-type Activation
    Weber, Jessica M.
    Longstreet, Ashley R.
    Jamison, Timothy F.
    ORGANOMETALLICS, 2018, 37 (16) : 2716 - 2722
12345