Stereoselective Palladium-Catalyzed C-F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki-Heck Reaction

被引：6
|
作者：
Wang, Yanhui [1 ]
Tsui, Gavin Chit [1 ]
机构：
[1] Chinese Univ Hong Kong, Dept Chem, Hong Kong 999077, Peoples R China
来源：
ORGANIC LETTERS | 2023年
关键词：
VINYLIC FLUORINES; ALKENES; ARYL;
D O I：
10.1021/acs.orglett.3c02452
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly diastereoselectivePd(0)-catalyzed Mizoroki-Heckreaction of gem-difluoroalkenes is described. Unlikepreviously reported C-F bond functionalization with organometallicreagents, this reaction takes place between two different alkenesto achieve a formal C-F and C-H bond cross-couplingvia a distinct pathway. Monofluorinated 1,3-diene products can besynthesized with control of the geometry of each alkene and good functionalgroup tolerability.
引用
收藏
页码：6217 / 6221
页数：5
相关论文
共 50 条
  • [1] Stereoselective Palladium-Catalyzed C-F Bond Alkynylation of Tetrasubstituted gem-Difluoroalkenes
    Ma, Qiao
    Wang, Yanhui
    Tsui, Gavin Chit
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11293 - 11297
  • [2] Stereoselective Palladium-Catalyzed C–F Bond Alkynylation of Tetrasubstituted gem-Difluoroalkenes
    Ma, Qiao
    Wang, Yanhui
    Tsui, Gavin Chit
    Advanced Materials, 2020, 132 (28): : 11389 - 11393
  • [3] Stereodivergent Palladium-Catalyzed C-F Bond Functionalization of gem-Difluoroalkenes
    Wang, Yanhui
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2024,
  • [4] Palladium-Catalyzed Stereoselective Hydrodefluorination of Tetrasubstituted gem-Difluoroalkenes
    Ma, Quo
    Liu, Caroline
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2020, 22 (13) : 5193 - 5197
  • [5] Stereoselective Synthesis of Difluorinated 1,3-Dienes via Palladium-Catalyzed C-F Bond Activation of Tetrasubstituted gem-Difluoroalkenes
    Wang, Yanhui
    Ma, Qiao
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2021, 23 (13) : 5241 - 5245
  • [6] Stereoselective Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Tetrasubstituted gem-Difluoroalkenes
    Li, Min
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2023, 26 (01) : 376 - 379
  • [7] Palladium-Catalyzed Stereoselective Defluorosilylation of gem-Difluoroalkenes for the Synthesis of Tetrasubstituted Monofluorinated Vinylsilanes
    Tsui, Gavin Chit
    Zong, Yuwei
    Luo, Ziwei
    ORGANIC LETTERS, 2023, 25 (13) : 2333 - 2337
  • [8] Stereoselective Rhodium(I)-Catalyzed C-F Bond Arylation of Tri-and Tetrasubstituted gem-Difluoroalkenes with Boronic Acids
    Tan, Hao
    Zong, Yuwei
    Tang, Yihan
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2023, 25 (05) : 877 - 882
  • [9] Palladium-Catalyzed Stereoselective C-F Bond Vinylation and Allylation of Tetrasubstituted gem-Difluoroalkenes via Stille Coupling: Synthesis of Monofluorinated 1,3-and 1,4-Dienes
    Li, Min
    Wang, Yanhui
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2021, 23 (20) : 8072 - 8076
  • [10] Nickel-Catalyzed Stereoselective Cascade C-F Functionalizations of gem-Difluoroalkenes
    Li, Xiaowei
    Li, Yuxiu
    Wang, Zemin
    Shan, Wenlong
    Liu, Ruihua
    Shi, Cong
    Qin, Hongyun
    Yuan, Leifeng
    Li, Xiangqian
    Shi, Dayong
    ACS CATALYSIS, 2023, 13 (03) : 2135 - 2141
12345