Preparation of functionalized aryl magnesium reagents by the addition of magnesium aryl thiolates and amides to arynes

被引:78
|
作者
Lin, WW [1 ]
Sapountzis, I [1 ]
Knochel, P [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
amination; arynes; Grignard reagents; heterocycles; thioethers;
D O I
10.1002/anie.200500443
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Reactive arynes, which are readily generated by the reaction of ortho-iocloarylsulfonates with iPrMgCl, undergo the smooth addition of various magnesium nucleophiles like magnesium thiolates, selenides, and amides. In all cases the resulting functionalized aryl magnesium species can be trapped by an electrophile leading to highly functionalized aromatic compounds (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4258 / 4261
页数:4
相关论文
共 50 条
  • [41] Preparation of polyfunctional pyridines by a palladium(-0)-catalyzed cross-coupling of functionalized aryl Grignard reagents
    Bonnet, W
    Mongin, F
    Trécourt, F
    Quéguiner, G
    Knochel, P
    TETRAHEDRON LETTERS, 2001, 42 (33) : 5717 - 5719
  • [42] Improved synthesis of aryl and alkyl phosphine oxides directly from phosphonates utilizing organo-magnesium reagents
    Kendall, Alexander J.
    Salazar, Chase A.
    Martino, Patrick F.
    Tyler, David R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [43] The use of aryl esters for the preparation of amides and derivatives of urea.
    Heubaum, U
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 : 2149 - 2150
  • [44] Synthesis of Functionalized Aryl Fluorides Using Organolithium Reagents in Flow Microreactors
    Nagaki, Aiichiro
    Uesugi, Yuki
    Kim, Heejin
    Yoshida, Jun-ichi
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (04) : 705 - 708
  • [45] Room temperature dehalogenation of (hetero)aryl halides with magnesium/methanol
    Jouha, Jabrane
    Khouili, Mostafa
    Hiebel, Marie-Aude
    Guillaumet, Gerald
    Suzenet, Franck
    TETRAHEDRON LETTERS, 2018, 59 (32) : 3108 - 3111
  • [46] FORMATION OF METHYLARYLCARBINOLS AS BY-PRODUCTS IN PREPARATION OF ARYL GRIGNARD REAGENTS
    BASS, KC
    CAPE, MJ
    COLLINGS, D
    CHEMISTRY & INDUSTRY, 1969, (11) : 326 - &
  • [47] Large-Scale Preparation of Aromatic Fluorides via Electrophilic Fluorination with Functionalized Aryl- or Heteroarylmagnesium Reagents
    Yamada, Shigeyuki
    Knochel, Paul
    SYNTHESIS-STUTTGART, 2010, (14): : 2490 - 2494
  • [48] The preparation of functionalized amines and amides using benzotriazole derivatives and organozinc reagents
    Katritzky, AR
    Strah, S
    Belyakov, SA
    TETRAHEDRON, 1998, 54 (25) : 7167 - 7178
  • [49] Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones
    Talero, Alexander Garay
    Martins, Bruna Simoes
    Burtoloso, Antonio C. B.
    ORGANIC LETTERS, 2018, 20 (22) : 7206 - 7211
  • [50] Nickel-Catalyzed Cross-Coupling of Non-Activated or Functionalized Aryl Halides with Aryl Grignard Reagents
    Xie, Lan-Gui
    Wang, Zhong-Xia
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (34) : 10332 - 10336