Iron-Catalyzed Cross-Coupling of N-Heterocyclic Chlorides and Bromides with Arylmagnesium Reagents

被引:79
作者
Kuzmina, Olesya M. [1 ]
Steib, Andreas K. [1 ]
Flubacher, Dietmar [2 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] Novartis Pharma AG, CH-4056 Basel, Switzerland
基金
欧洲研究理事会;
关键词
ARYL GRIGNARD-REAGENTS; SECONDARY ALKYL-HALIDES; BETA-HYDROGENS; BOND FORMATION; COMPLEX; TOSYLATES; EFFICIENT; OXIDANT; LIGAND; SALTS;
D O I
10.1021/ol302136c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, practical iron salt catalyzed procedure allows fast cross-couplings of N-heterocyclic chlorides and bromides with various electron-rich and -poor arylmagnesium reagents. A solvent mixture of THF and tBuOMe is found to be essential for achieving high yields mainly by avoiding homocoupling side reactions.
引用
收藏
页码:4818 / 4821
页数:4
相关论文
共 77 条
  • [21] Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions
    Czaplik, Waldemar Maximilian
    Mayer, Matthias
    Cvengros, Jan
    Jacobi von Wangelin, Axel
    [J]. CHEMSUSCHEM, 2009, 2 (05) : 396 - 417
  • [22] Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling
    Czaplik, Waldemar Maximilian
    Mayer, Matthias
    Jacobi von Wangelin, Axel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) : 607 - 610
  • [23] Enthaler S., 2008, Angew. Chem, V120, P3363
  • [24] Sustainable metal catalysis with iron: From rust to a rising star?
    Enthaler, Stephan
    Junge, Kathrin
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) : 3317 - 3321
  • [25] MIXED COUPLING BETWEEN VINYLIC SULFONES AND GRIGNARD-REAGENTS IN THE PRESENCE OF SALTS OF TRANSITION-METALS - STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED OLEFINS
    FABRE, JL
    JULIA, M
    VERPEAUX, JN
    [J]. TETRAHEDRON LETTERS, 1982, 23 (24) : 2469 - 2472
  • [26] KHARASCH-TYPE HOMOCOUPLING REACTION CATALYZED BY IRON COMPLEXES
    FELKIN, H
    MEUNIER, B
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 146 (02) : 169 - 178
  • [27] Preparation, structure, and reactivity of nonstabilized organoiron compounds.: Implications for iron-catalyzed cross coupling reactions
    Fuerstner, Alois
    Martin, Ruben
    Krause, Helga
    Seidel, Guenter
    Goddard, Richard
    Lehmann, Christian W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8773 - 8787
  • [28] From Oblivion into the Limelight: Iron (Domino) Catalysis
    Fuerstner, Alois
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) : 1364 - 1367
  • [29] Fürstner A, 2002, ANGEW CHEM INT EDIT, V41, P609
  • [30] Advances in iron catalyzed cross coupling reactions
    Fürstner, A
    Martin, R
    [J]. CHEMISTRY LETTERS, 2005, 34 (05) : 624 - 629