Domino gold-catalyzed rearrangement and fluorination of propargyl acetates

被引:116
|
作者
de Haro, Teresa [1 ]
Nevado, Cristina [1 ]
机构
[1] Univ Zurich, Inst Organ Chem, CH-8006 Zurich, Switzerland
关键词
ALPHA-FLUOROENONES; CYCLIZATION;
D O I
10.1039/c002679d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A combination of IPrAuNTf2 as catalyst in the presence of Selectfluor has been successfully used for the high yielding synthesis of alpha-fluoroenones via 1,3-acyloxy rearrangement of propargyl acetates followed by Csp(2)-F bond formation, likely involving a redox Au(I)/Au(III) catalytic cycle.
引用
收藏
页码:248 / 249
页数:2
相关论文
共 50 条
  • [31] Gold-catalyzed rearrangement of substituted allyl aryl ethers
    Vyvyan, James R.
    Dimmitt, Heidi E.
    Griffith, Jennifer K.
    Steffens, Laura D.
    Swanson, Rebecca A.
    TETRAHEDRON LETTERS, 2010, 51 (50) : 6666 - 6669
  • [32] Gold-Catalyzed Reaction of Propargyl Esters and Alkynylsilanes: Synthesis of Vinylallene Derivatives through a Twofold 1,2-Rearrangement
    Bernardo, Olaya
    Gonzalez-Pelayo, Silvia
    Fernandez, Israel
    Lopez, Luis A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (48) : 25258 - 25262
  • [33] Gold-catalyzed efficient formation of α,β-unsaturated ketones from propargylic acetates
    Yu, Meng
    Li, Guotao
    Wang, Shaozhong
    Zhang, Liming
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (06) : 871 - 875
  • [34] Gold-catalyzed efficient preparation of linear α-haloenones from propargylic acetates
    Yu, Meng
    Zhang, Guozhu
    Zhang, Liming
    TETRAHEDRON, 2009, 65 (09) : 1846 - 1855
  • [35] Gold-catalyzed efficient preparation of linear α-iodoenones from propargylic acetates
    Yu, Meng
    Zhang, Guozhu
    Zhang, Liming
    ORGANIC LETTERS, 2007, 9 (11) : 2147 - 2150
  • [36] Gold-catalyzed fluorination of alkynes/allenes: mechanistic explanations and reaction scope
    Roy, Deblina Singha
    Tanwer, Yogesh Bhaskar Singh
    Patra, Snigdha Rani
    Kumar, Shivam
    Bhunia, Sabyasachi
    Das, Debjit
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 23 (01) : 11 - 35
  • [37] Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O-Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene
    Barbazanges, Marion
    Gimbert, Yves
    Fensterbank, Louis
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 3297 - 3302
  • [38] Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to α-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B
    Ghosh, Nayan
    Nayak, Sanatan
    Sahoo, Akhila K.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02): : 500 - 511
  • [39] Kinetic Analysis of Domino Catalysis: A Case Study on Gold-Catalyzed Arylation
    Ball, Liam T.
    Corrie, Tom J. A.
    Cresswell, Alexander J.
    Lloyd-Jones, Guy C.
    ACS CATALYSIS, 2020, 10 (18) : 10420 - 10426
  • [40] Gold-catalyzed rearrangement of propargylic tert-butyl carbonates
    Buzas, Andrea K.
    Istrate, Florin M.
    Gagosz, Fabien
    TETRAHEDRON, 2009, 65 (09) : 1889 - 1901