Palladium-Catalyzed Tandem Fluorination and Cyclization of Enynes

被引：86
作者：
Peng, Haihui [1 ]
Liu, Guosheng [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 04期
关键词：
ARYL FLUORIDES; BOND FORMATION; STEREOSELECTIVE-SYNTHESIS; METAL CATALYSIS; ALKYNES; REACTIVITY; CONVERSION; MOLECULES; STATE;
D O I：
10.1021/ol103039x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel palladium-catalyzed tandem fluorination and cyclization of enynes has been developed. A favorable cis-fluoropalladation is proposed as a key step to construct a vinyl-F bond, and the final C-5p3-Pd bond is reduced by alcohol. This transformation represents an efficient road to synthesize fluorinated lactams.
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收藏
页码：772 / 775
页数：4
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共 43 条
  • [1] Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes
    Akana, Jennifer A.
    Bhattacharyya, Koyel X.
    Mueller, Peter
    Sadighi, Joseph P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) : 7736 - +
  • [2] Efficient Synthesis of Aryl Fluorides
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2219 - 2222
  • [3] Nucleophilic reactivity towards electrophilic fluorinating agents:: reaction with N-fluorobenzenesulfonimide ((PhSO2)2NF)
    Antelo, JM
    Crugeiras, J
    Leis, JR
    Ríos, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (10): : 2071 - 2076
  • [4] Banks R. E., 1994, ORGANOFLUORINE CHEM
  • [5] Transition-Metal-Mediated Reactions for Csp2-F Bond Construction: The State of Play
    Brown, John M.
    Gouverneur, Veronique
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) : 8610 - 8614
  • [6] Fagnou K, 2002, ANGEW CHEM INT EDIT, V41, P26, DOI 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO
  • [7] 2-9
  • [8] Carbon-Fluorine Bond Formation for the Synthesis of Aryl Fluorides
    Furuya, Takeru
    Klein, Johannes E. M. N.
    Ritter, Tobias
    [J]. SYNTHESIS-STUTTGART, 2010, (11): : 1804 - 1821
  • [9] Palladium-mediated fluorination of arylboronic acids
    Furuya, Takeru
    Kaiser, Hanns Martin
    Ritter, Tobias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) : 5993 - 5996
  • [10] Straightforward conversion of alcohols into dibenzenesulfonimides
    Giovanelli, Emerson
    Doris, Eric
    Rousseau, Bernard
    [J]. TETRAHEDRON LETTERS, 2006, 47 (48) : 8457 - 8458
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