Visible Light-Induced Pd-Catalyzed Heck Reactions

被引:2
|
作者
Xu Wei [1 ]
Zhai Hongbin [1 ,2 ]
Cheng Bin [1 ]
Wang Taimin [1 ]
机构
[1] Shenzhen Polytech, Inst Marine Biomed, Shenzhen 518055, Guangdong, Peoples R China
[2] Peking Univ, Shenzhen Grad Sch, State Key Lab Chem Oncogen, Shenzhen 518055, Guangdong, Peoples R China
关键词
visible light; Pd-1; species; radical; single electron transfer; Heck reaction; HALIDES;
D O I
10.6023/cjoc202303013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heck reaction is regarded as one of the most powerful and practical synthetic tools to construct C-C bonds, and has gained increasingly widespread applications in the synthesis of various functional molecules over the past decades. As an emerging strategy for the formation of C-C bonds, visible light-induced Pd-catalyzed Heck reaction has tremendously extended the scope of substrates, in both aspects of nucleophiles and electrophiles. This unique transformation, triggered by photoexcited Pd-0 and mechanistically involving hybrid radical-Pd-1 species, features mild conditions, excellent functional compatibility and transformational diversity, which greatly complements classical Heck reaction catalyzed by ground-state Pd complexes. These advantages will render visible light-induced Heck reaction widespread applications in the synthesis of functional molecules and late-stage modification of structurally complex compounds. According to the species of nucleophiles/electrophiles and types of cascade reactions, visible light-induced Heck reactions are logically classified, and some of the elusive reaction mechanisms are also illustrated.
引用
收藏
页码:3035 / 3054
页数:20
相关论文
共 58 条
  • [1] Photocatalytic Palladium-Catalyzed Fluoroalkylation of Styrene Derivatives
    Adamik, Reka
    Foldesi, Tamas
    Novak, Zoltan
    [J]. ORGANIC LETTERS, 2020, 22 (20) : 8091 - 8095
  • [2] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [3] Three-component three-bond forming cascade via palladium photoredox catalysis
    Bellotti, Peter
    Koy, Maximilian
    Gutheil, Christian
    Heuvel, Steffen
    Glorius, Frank
    [J]. CHEMICAL SCIENCE, 2021, 12 (05) : 1810 - 1817
  • [4] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
    CABRI, W
    CANDIANI, I
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
  • [5] Visible-light-driven palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade
    Chen, Li
    Guo, Li-Na
    Liu, Shuai
    Liu, Le
    Duan, Xin-Hua
    [J]. CHEMICAL SCIENCE, 2021, 12 (05) : 1791 - 1795
  • [6] Visible-Light-Driven Palladium-Catalyzed Radical Tandem Dearomatization of Indoles with Unactivated Alkenes
    Chen, Su
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    Sharma, Upendra K.
    [J]. ORGANIC LETTERS, 2022, 24 (05) : 1213 - 1218
  • [7] Transition Metal-Catalyzed Organic Reactions under Visible Light: Recent Developments and Future Perspectives
    Cheng, Wan-Min
    Shang, Rui
    [J]. ACS CATALYSIS, 2020, 10 (16) : 9170 - 9196
  • [8] Visible Light-Induced Transition Metal Catalysis
    Cheung, Kelvin Pak Shing
    Sarkar, Sumon
    Gevorgyan, Vladimir
    [J]. CHEMICAL REVIEWS, 2022, 122 (02) : 1543 - 1625
  • [9] Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond
    Cheung, Kelvin Pak Shing
    Kurandina, Daria
    Yata, Tetsuji
    Gevorgyan, Vladimir
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (22) : 9932 - 9937
  • [10] Catalysis with Palladium Complexes Photoexcited by Visible Light
    Chuentragool, Padon
    Kurandina, Daria
    Gevorgyan, Vladimir
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (34) : 11586 - 11598