Improved Air-Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross-Couplings

被引：80
作者：
Stathakis, Christos I. [1 ]
Bernhardt, Sebastian [1 ]
Quint, Valentin [1 ]
Knochel, Paul [1 ]
机构：
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 37期
基金：
欧洲研究理事会;
关键词：
cross-coupling; heterocycles; metalation; organozinc reagents; palladium; ORGANOZINC REAGENTS; ARYL; HALIDES; MAGNESIUM; FUNCTIONALIZATION; PRECATALYST; CATALYSIS; ARENES; BASES; NHC;
D O I：
10.1002/anie.201204526
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Directed metalation using TMPMgCl·LiCl (TMP=2,2,6,6- tetramethylpiperidide) and subsequent transmetalation with Zn(OPiv) 2 leads to aryl and heteroaryl zinc pivalates. After solvent evaporation, easy-to-handle fine powders are obtained that retain most of their activity (>85 %) when exposed to air for 4 h. They smoothly undergo Negishi cross-couplings, and technical-grade solvents can be used without significant loss of yield. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9428 / 9432
页数：5
相关论文
共 43 条
  • [1] [Anonymous], 2010, ANGEW CHEM
  • [2] [Anonymous], 2008, ANGEW CHEM
  • [3] Expanding Mg-Zn Hybrid Chemistry: Inorganic Salt Effects in Addition Reactions of Organozinc Reagents to Trifluoroacetophenone and the Implications for a Synergistic Lithium-Magnesium-Zinc Activation
    Armstrong, David R.
    Clegg, William
    Garcia-Alvarez, Pablo
    Kennedy, Alan R.
    McCall, Matthew D.
    Russo, Luca
    Hevia, Eva
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (30) : 8333 - 8341
  • [4] Bernhardt S., 2011, ANGEW CHEM, V123, P9372
  • [5] Preparation of Solid Salt-Stabilized Functionalized Organozinc Compounds and their Application to Cross-Coupling and Carbonyl Addition Reactions
    Bernhardt, Sebastian
    Manolikakes, Georg
    Kunz, Thomas
    Knochel, Paul
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9205 - 9209
  • [6] Calimsiz S., 2010, Angewandte Chemie, V122, P2058
  • [7] Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls
    Calimsiz, Selcuk
    Sayah, Mahmoud
    Mallik, Debasis
    Organ, Michael G.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (11) : 2014 - 2017
  • [8] Synthesis of Fully Substituted Pyrazoles via Regio- and Chemoselective Metalations
    Despotopoulou, Christina
    Klier, Lydia
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3326 - 3329
  • [9] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS
    FARINA, V
    KRISHNAN, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9585 - 9595
  • [10] Haag B., 2011, ANGEW CHEM, V123, P9968
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