Classical Reagents: New Surprises in Palladium-Catalyzed C-C Coupling Reactions

被引:30
|
作者
Lindhardt, Anders T. [1 ,2 ]
Skrydstrup, Troels [1 ,2 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Insoluble Prot Struct inSPIN, DK-8000 Aarhus, Denmark
[2] Aarhus Univ, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus, Denmark
基金
新加坡国家研究基金会;
关键词
alkynes; hydride elimination; C-C coupling reactions; hydropalladation; palladium;
D O I
10.1002/chem.200800608
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
From investigations on a relatively simple concept to identify conditions for promoting Mizoroki-Heck reactions with vinyl tosylates and phosphates, two serendipitous discoveries were made concerning new properties of palladium as a catalyst. In the first case, beta-hydride eliminations well known for alkyl metal complexes were found to be equally feasible with alkenyl metal compounds. And secondly, conditions were found for promoting intermolecular ene-yne couplings via a Pd-II-H intermediate. This coupling reactions represents an atom economical Mizoroki-Heck type reaction.
引用
收藏
页码:8756 / 8766
页数:11
相关论文
共 50 条
  • [31] L-Arginine as a base and ligand for the palladium-catalyzed C-C and C-N cross-coupling reactions in aqueous media
    Veisi, Hojat
    Biabri, Parisa Mohammadi
    Falahi, Homeyra
    [J]. TETRAHEDRON LETTERS, 2017, 58 (35) : 3482 - 3486
  • [32] Theoretical Studies on a New Class of C-C Bond Formation: Palladium-Catalyzed Reactions of α-Diazocarbonyl Compounds with Allylic Esters
    Wang, Hongliang
    Yang, Xu
    Liu, Yuxia
    Bi, Siwei
    [J]. ORGANOMETALLICS, 2014, 33 (06) : 1404 - 1415
  • [33] Palladium-Catalyzed C-C Bonds Formation Reactions via Selective C-H Bonds Functionalization
    Li Hu
    Shi Zhangjie
    [J]. PROGRESS IN CHEMISTRY, 2010, 22 (07) : 1414 - 1433
  • [34] C-C Coupling Reactions in Water Catalyzed by Palladium(II) Supported on Microporous Organic Polymer
    Kong, Shengnan
    Malik, Abaid Ullah
    Qian, Xuefeng
    Shu, Mouhai
    Xiao, Wende
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (02) : 432 - 442
  • [35] Efficient palladium-catalyzed Suzuki C-C coupling of novel urea/thiourea-based quinazolines
    Patel, Amit B.
    Chikhalia, Kishor H.
    Kumari, Premlata
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (05) : 2665 - 2674
  • [36] Palladium-Catalyzed Migratory Insertion of Carbenes and C-C Cleavage of Cycloalkanecarboxamides
    Zhang, Peng
    Zeng, Jia
    Pan, Ping
    Zhang, Xue-Jing
    Yan, Ming
    [J]. ORGANIC LETTERS, 2022, 24 (02) : 536 - 541
  • [37] Palladium-Catalyzed C-C Bond Activation/Suzuki Reaction of Methylenecyclobutanes
    Chen, Xiao-Bing
    Li, Li
    Yang, Wan-Chun
    Song, Kun-Long
    Wu, Bin
    Gan, Wan-Er
    Cao, Jian
    Xu, Li-Wen
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (06) : 1611 - 1615
  • [38] Palladium-Catalyzed Asymmetric C-C Bond Activation/Carbonylation of Cyclobutanones
    Chen, Long
    Shi, Cong
    Li, Wei
    Li, Bo
    Zhu, Jie
    Lin, Aijun
    Yao, Hequan
    [J]. ORGANIC LETTERS, 2022, : 9157 - 9162
  • [39] Palladium metal catalysts in Heck C-C coupling reactions
    Biffis, A
    Zecca, M
    Basato, M
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 173 (1-2) : 249 - 274
  • [40] Palladium-Catalyzed C-C Coupling/C-H Activation: Formation of Isoindolinone-Fused Heterocyclic Compounds
    Hu, Yimin
    Ren, Dong
    Zhang, Lidong
    Lin, Xiangang
    Wan, Jing
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) : 4454 - 4459