Aminoalkoxide-mediated formation and stabilization of phenylpyridyllithium: Straightforward access to phenylpyridine derivatives

被引:13
作者
Gros, P [1 ]
Fort, Y [1 ]
机构
[1] Univ Nancy 1, UMR CNRS 7565, Fac Sci, F-54506 Vandoeuvre Les Nancy, France
关键词
D O I
10.1021/jo026706o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It is shown that lithium aggregates promoted the efficient metalation of phenylpyridines and stabilization of phenylpyridyllithium. The BuLi-LiDMAE superbase prevented dimerization or nucleophilic addition encountered with t-BuLi or n-BuLi. The reported selective pyridine ring lithiation of 2-, 3-, and 4-phenylpyridine a to nitrogen opens a straightforward access to their derivatives.
引用
收藏
页码:2028 / 2029
页数:2
相关论文
共 19 条
[1]  
Alami M, 2001, EUR J ORG CHEM, V2001, P4207
[2]  
CHAPMAN GM, 2002, J CHEM SOC P1, V5, P581
[3]   Unusual C-6 lithiation of 2-chloropyridine-mediated by BuLi-Me2N(CH2)2OLi.: New access to 6-functional-2-chloropyridines and chloro-bis-heterocycles [J].
Choppin, S ;
Gros, P ;
Fort, Y .
ORGANIC LETTERS, 2000, 2 (06) :803-805
[4]   NEW SYNTHETIC ROUTES TO 3-ARYL-2-CHLOROPYRIDINES, 5-ARYL-2-CHLOROPYRIDINES, AND 6-ARYL-2-CHLOROPYRIDINES [J].
CHURCH, R ;
TRUST, R ;
ALBRIGHT, JD ;
POWELL, DW .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3750-3758
[5]  
DEGUSSA HB, 1981, ALDRICHIM ACTA, V14, P13
[6]   Reaction of organolithium reagents with cyclorhenated and cyclomanganated (η6-arene)tricarbonylchromium complexes:: Structural characterization of a new benzoylrhenate intermediate and selective ortho-acetylation of (η6-arene) tricarbonylchromium complexes [J].
Djukic, JP ;
Maisse, A ;
Pfeffer, M ;
Dötz, KH ;
Nieger, M .
ORGANOMETALLICS, 1999, 18 (15) :2786-2790
[7]  
Gros P, 2002, EUR J ORG CHEM, V2002, P3375
[8]   Lithiation of 2-heterosubstituted pyridines with BuLi-LiDMAE: Evidence for regiospecificity at C-6 [J].
Gros, P ;
Choppin, S ;
Mathieu, J ;
Fort, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :234-237
[9]   ALKENE AND ALKYNE INSERTION REACTIONS OF CATIONIC CP2ZR(ETA-2-PYRIDYL)(L)+ COMPLEXES - ZIRCONIUM-MEDIATED FUNCTIONALIZATION OF PYRIDINES [J].
GURAM, AS ;
JORDAN, RF .
ORGANOMETALLICS, 1991, 10 (10) :3470-3479
[10]  
Lim Y.-G., 1996, J CHEM SOC P1, V17, P2201