Functionalization of a non activated C-H bond: Fluorination of vindoline at C-20 in superacids

被引：14
|
作者：
Berrier, C
Jacquesy, JC
Jouannetaud, MP
Lafitte, C
Vidal, Y
Zunino, F
Fahy, J
Duflos, A
机构：
[1] Univ Poitiers, Lab Synth & Reactiv Substances Nat, UMR 6514, F-86022 Poitiers, France
[2] Ctr Rech Pierre Fabre, Div Chim Med 5, F-81106 Castres, France
来源：
TETRAHEDRON | 1998年 / 54卷 / 45期
关键词：
D O I：
10.1016/S0040-4020(98)00845-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of vindoline 1a with NBS, NCS, H2O2 in HF-SbF5 yields 7 beta substituted (Br, Cl or OH)-20-fluoro-6,7-dihydrovindolines. These results imply reaction of the electrophile (Br+, Cl+ and OH+ equivalent) on the beta-face of C-6-C-7 double bond to give oniums ions, followed by a 1,3-hydride shift from C-20 to Cd, and fluorination of the resulting ion. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：13761 / 13770
页数：10
相关论文
共 50 条
  • [21] Nickel complexes for catalytic C-H bond functionalization
    Johnson, S. A.
    DALTON TRANSACTIONS, 2015, 44 (24) : 10905 - 10913
  • [22] Development of new C-H bond functionalization reactions
    Sanford, Melanie
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [23] Rapid assembly of heterocycles by C-H bond functionalization
    Ellman, Jonathan A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [24] Drug Synthesis via C-H Bond Functionalization
    Gong Hao
    Yang Yiwen
    Kuang Chunxiang
    PROGRESS IN CHEMISTRY, 2014, 26 (04) : 592 - 608
  • [25] Metal-Catalyzed C-H Bond Functionalization
    Baudoin, Olivier
    TETRAHEDRON, 2013, 69 (22) : 4370 - 4370
  • [26] Catalytic C-H Bond Stannylation: A New Regioselective Pathway to C-Sn Bonds via C-H Bond Functionalization
    Doster, Meghan E.
    Hatnean, Jillian A.
    Jeftic, Tamara
    Modi, Sunjay
    Johnson, Samuel A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) : 11923 - 11925
  • [27] Micellar Catalysis as a Tool for C-H Bond Functionalization toward C-C Bond Formation
    Borrego, Elena
    Caballero, Ana
    Perez, Pedro J.
    ORGANOMETALLICS, 2022, 41 (22) : 3084 - 3098
  • [28] C-H Functionalization
    Doyle, Michael P.
    Goldberg, Karen I.
    ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 777 - 777
  • [29] C-H Functionalization
    Davies, Huw M. L.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1552 - 1553
  • [30] C-H functionalization
    White, M. Christina
    CHEMICAL & ENGINEERING NEWS, 2021, 99 (10) : 3 - 3
12345