Enantioselective Palladium-Catalyzed Oxidative β,β-Fluoroarylation of α,β-Unsaturated Carbonyl Derivatives

被引:61
|
作者
Miro, Javier [1 ]
del Pozo, Carlos [1 ]
Toste, F. Dean [2 ]
Fustero, Santos [1 ,3 ]
机构
[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[3] Ctr Invest Principe Felipe, Lab Mol Organ, Valencia 46012, Spain
关键词
alkenes; fluorine; palladium; reaction mechanisms; synthetic methods; ALPHA-AMINO-ACIDS; C-H BONDS; BENZYLIC FLUORINATION; NUCLEOPHILIC FLUORINATION; SELECTIVE FLUORINATION; REDUCTIVE ELIMINATION; PHASE-TRANSFER; BORONIC ACIDS; FLUORIDE; ALKENES;
D O I
10.1002/anie.201603046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The site-selective palladium-catalyzed three-component coupling of deactivated alkenes, arylboronic acids, and N-fluorobenzenesulfonimide is disclosed herein. The developed methodology establishes a general, modular, and step-economical approach to the stereoselective beta-fluorination of alpha,beta-unsaturated systems.
引用
收藏
页码:9045 / 9049
页数:5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Enantioselective 1,1-Fluoroarylation of Aminoalkenes
    He, Ying
    Yang, Zhenyu
    Thornbury, Richard T.
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (38) : 12207 - 12210
  • [2] Palladium-Catalyzed Intramolecular Fluoroarylation of Alkenes
    Yang, Wencheng
    Qi, Xiaoxu
    Chen, Pinhong
    Liu, Guosheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (01) : 122 - 128
  • [3] Palladium-Catalyzed Enantioselective γ-Arylation of β,γ-Unsaturated Butenolides
    Li, Sanliang
    Chen, Qiaoyu
    Yang, Junfeng
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (23)
  • [4] Palladium-catalyzed directed intermolecular fluoroarylation of chromenes
    Fernandes, Talita de A.
    Thornbury, Richard T.
    Talbot, Eric P. A.
    McKenna, Jeffrey M.
    Toste, F. Dean
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [5] Palladium-Catalyzed Fluoroarylation of gem-Difluoroalkenes
    Tang, Hai-Jun
    Lin, Ling-Zhi
    Feng, Chao
    Loh, Teck-Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (33) : 9872 - 9876
  • [6] Palladium-catalyzed enantioselective alkenylation of alkenylbenzene derivatives
    Chen, Zhi-Min
    Liu, Jianbo
    Guo, Jing-Yao
    Loch, Maximilian
    DeLuca, Ryan J.
    Sigman, Matthew S.
    CHEMICAL SCIENCE, 2019, 10 (30) : 7246 - 7250
  • [7] Recent advances in the synthesis of carbonyl compounds by palladium-catalyzed oxidative carbonylation reactions of unsaturated substrates
    Gabriele, B
    Salerno, G
    Costa, M
    Chiusoli, GP
    CURRENT ORGANIC CHEMISTRY, 2004, 8 (10) : 919 - 946
  • [8] Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes
    Talbot, Eric P. A.
    Fernandes, Talita de A.
    McKenna, Jeffrey M.
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) : 4101 - 4104
  • [9] Design and Synthesis of TY-Phos and Application in Palladium-Catalyzed Enantioselective Fluoroarylation ofgem-Difluoroalkenes
    Lin, Tao-Yan
    Pan, Zhangjin
    Tu, Youshao
    Zhu, Shuai
    Wu, Hai-Hong
    Liu, Yu
    Li, Zhiming
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (51) : 22957 - 22962
  • [10] Palladium-catalyzed desulfitative addition of sodium sulfinates with α,β-unsaturated carbonyl compounds
    Chen, Wen
    Zhou, Xianya
    Xiao, Fuhong
    Luo, Jiaying
    Deng, Guo-Jun
    TETRAHEDRON LETTERS, 2012, 53 (33) : 4347 - 4350