First regioselective ortho-lithiation induced by a 2-chloropyridyl group complexation

被引:25
作者
Fort, Y [1 ]
Rodrigues, AL [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/jo026788g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It is shown that t-BuLi in Et2O promotes an exclusive regioselective metalation of 2-aryl-6-chloropyridine compounds at the aromatic ortho position demonstrating that the 2-chloropyridyl moiety may be considered as a directing group. This functionally directed metalation group was successfully used for the selective lithiation of substituted aromatics and for the straightforward preparation of new N,P ligands.
引用
收藏
页码:4918 / 4922
页数:5
相关论文
共 47 条
[1]   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
[2]   STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].
BEAK, P ;
MEYERS, AI .
ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363
[3]   METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].
BEAK, P ;
ZAJDEL, WJ ;
REITZ, DB .
CHEMICAL REVIEWS, 1984, 84 (05) :471-523
[4]   Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].
Beak, P ;
Basu, A ;
Gallagher, DJ ;
Park, YS ;
Thayumanavan, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560
[5]   DIASTEREOISOMERIC ATROPISOMERS FROM THE ADDITION OF LITHIATED N,N-DIALKYL-1-NAPHTHAMIDES TO ALDEHYDES [J].
BOWLES, P ;
CLAYDEN, J ;
TOMKINSON, M .
TETRAHEDRON LETTERS, 1995, 36 (50) :9219-9222
[6]   Nickel-mediated amination chemistry.: Part 2:: Selective N-arylation or N,N′-diarylation of piperazine [J].
Brenner, E ;
Schneider, R ;
Fort, Y .
TETRAHEDRON LETTERS, 2000, 41 (16) :2881-2884
[7]   Nickel-catalysed couplings of aryl chlorides with secondary amines and piperazines [J].
Brenner, E ;
Schneider, R ;
Fort, Y .
TETRAHEDRON, 1999, 55 (44) :12829-12842
[8]   New efficient nickey(0) catalysed amination of aryl chlorides [J].
Brenner, E ;
Fort, Y .
TETRAHEDRON LETTERS, 1998, 39 (30) :5359-5362
[9]   COMPLEXES WITH A PINCERS - 2,6-DIPHENYLPYRIDINE AS TWOFOLD-DEPROTONATED (C OR N OR C) TERDENTATE LIGAND IN C,C-TRANS-DEPROTONATED, AND AS MONO-DEPROTONATED (C OR N) CHELATE LIGAND IN CHIRAL C,C-CIS-COMPLEXES OF PLATINUM(II) AND PALLADIUM(II) [J].
CORNIOLEYDEUSCHEL, C ;
WARD, T ;
VONZELEWSKY, A .
HELVETICA CHIMICA ACTA, 1988, 71 (01) :130-133
[10]   Nickel (0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines [J].
Desmarets, C ;
Schneider, R ;
Fort, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3029-3036