Synthesis and reactivity of lithium tri(quinolinyl)magnesates

被引：60
作者：
Dumouchel, S [1 ]
Mongin, F [1 ]
Trécourt, F [1 ]
Quéguiner, G [1 ]
机构：
[1] IRCOF, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France
来源：
TETRAHEDRON | 2003年 / 59卷 / 43期
关键词：
quinolines; ate complexes; in situ IR; cross-coupling;
D O I：
10.1016/j.tet.2003.06.001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-, 3- and 4-Bromoquinolines, were converted to the corresponding lithium tri(quinolinyl)magnesates at -10degreesC when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：8629 / 8640
页数：12
相关论文
共 83 条
[1]   PREPARATION OF EXTENDED DI(4-PYRIDYL)THIOPHENE OLIGOMERS [J].
ALBERS, WM ;
CANTERS, GW ;
REEDIJK, J .
TETRAHEDRON, 1995, 51 (13) :3895-3904
[2]   SYNTHESIS AND EASY RACEMIZATION OF AN ATROPISOMERICALLY CHIRAL PHOSPHINAMINE [J].
ALCOCK, NW ;
BROWN, JM ;
PEARSON, M ;
WOODWARD, S .
TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :17-20
[3]   Mechanistic and kinetic studies of palladium catalytic systems [J].
Amatore, C ;
Jutand, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278
[4]  
[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23
[5]   STEREOSELECTIVE ORGANOMETALLIC ALKYLATION REACTIONS .3. ATE COMPLEX ADDITION TO CYCLIC AND BICYCLIC KETONES [J].
ASHBY, EC ;
CHAO, LC ;
LAEMMLE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (22) :3258-3263
[6]  
BIZOT J, 1967, B SOC CHIM FR, P151
[7]  
Böhm VPW, 2000, ANGEW CHEM INT EDIT, V39, P1602, DOI 10.1002/(SICI)1521-3773(20000502)39:9<1602::AID-ANIE1602>3.0.CO
[8]  
2-N
[9]  
Böhm VPW, 2001, ANGEW CHEM INT EDIT, V40, P3387
[10]  
Bonnet V, 2002, SYNLETT, P1008
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