Directed meta-metalation using alkali-metal-mediated zincation

被引:82
作者
Armstrong, David R.
Clegg, William
Dale, Sophie H.
Hevia, Eva
Hogg, Lorna M.
Honeyman, Gordon W.
Mulvey, Robert E.
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
[2] Newcastle Univ, Sch Nat Sci Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
anilides; deprotonation; metalation; sodium; zincation;
D O I
10.1002/anie.200600720
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Move over directed ortho-metalation, here comes directed meto-metalation. The unprecedented meto-zincation of two anilides by a synergic mixed sodium/zinc dialkyl-amide base is presented. The orientation of the deprotonation of the anilides is remarkably switched to the meta site using this heterometallic mixed-metal system. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3775 / 3778
页数:4
相关论文
共 24 条
  • [1] Selective meta-deprotonation of toluene by using alkali-metal-mediated magnesiation
    Andrikopoulos, PC
    Armstrong, DR
    Graham, DV
    Hevia, E
    Kennedy, AR
    Mulvey, RE
    O'Hara, CT
    Talmard, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) : 3459 - 3462
  • [2] A homologous series of regioselectively tetradeprotonated group 8 metallocenes: New inverse crown ring compounds synthesized via a mixed sodium-magnesium tris(diisopropylamide) synergic base
    Andrikopoulos, PC
    Armstrong, DR
    Clegg, W
    Gilfillan, CJ
    Hevia, E
    Kennedy, AR
    Mulvey, RE
    O'Hara, CT
    Parkinson, JA
    Tooke, DM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) : 11612 - 11620
  • [3] ANDRIKOPOULOS PC, 2005, ANGEW CHEM, V117, P3525
  • [4] Baston E, 2001, EUR J ORG CHEM, V2001, P3985
  • [5] DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS
    BEAK, P
    SNIECKUS, V
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) : 306 - 312
  • [6] ARENE-METAL COMPLEXES .13. REACTION OF SUBSTITUTED (BENZENE)TRICARBONYLCHROMIUM COMPLEXES WITH NORMAL-BUTYLLITHIUM
    CARD, RJ
    TRAHANOVSKY, WS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13) : 2560 - 2566
  • [7] Clayden J., 2002, ORGANOLITHIUMS SELEC
  • [8] Hartung C. G., 2002, MODERN ARENE CHEM, V34, P330, DOI DOI 10.1002/3527601767.CH10
  • [9] HESS C, 2005, EUR J ORG CHEM, P5236
  • [10] Bromine-magnesium exchange of 5-bromo-2-picoline via an organomagnesium complex nBu2iPrMgLi:: a new preparation methodology of functionalized picolines under noncryogenic conditions
    Kii, S
    Akao, A
    Iida, T
    Mase, T
    Yasuda, N
    [J]. TETRAHEDRON LETTERS, 2006, 47 (12) : 1877 - 1879