Directed meta-metalation using alkali-metal-mediated zincation

被引:83
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 [J].
Andrikopoulos, PC ;
Armstrong, DR ;
Graham, DV ;
Hevia, E ;
Kennedy, AR ;
Mulvey, RE ;
O'Hara, CT ;
Talmard, C .
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 [J].
Andrikopoulos, PC ;
Armstrong, DR ;
Clegg, W ;
Gilfillan, CJ ;
Hevia, E ;
Kennedy, AR ;
Mulvey, RE ;
O'Hara, CT ;
Parkinson, JA ;
Tooke, DM .
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 [J].
BEAK, P ;
SNIECKUS, V .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312
[6]   ARENE-METAL COMPLEXES .13. REACTION OF SUBSTITUTED (BENZENE)TRICARBONYLCHROMIUM COMPLEXES WITH NORMAL-BUTYLLITHIUM [J].
CARD, RJ ;
TRAHANOVSKY, WS .
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 [J].
Kii, S ;
Akao, A ;
Iida, T ;
Mase, T ;
Yasuda, N .
TETRAHEDRON LETTERS, 2006, 47 (12) :1877-1879