Mixed Mg/Li amides of the type R2NMgCl•LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds

被引：423

作者：

Krasovskiy, Arkady ^{[1
]}

Krasovskaya, Valeria ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 18期

关键词：

amides; Ggrignard reagents; heterocycles functionalization; lithium chloride; magnesium amides; mixed bases; regioselective metalation;

D O I：

10.1002/anie.200504024

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Two are better than one: Mixed lithium-magnesium complexes of the type R2NMgCl·LiCl are kinetically highly active bases that convert a range of polyfunctional aromatic and heteroaromatic substrates into the corresponding magnesiated derivatives with high regioselectivity. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2958 / 2961

页数：4

共 50 条

[1] Deprotonation of chloropyridines using lithium magnesates [J].

Awad, H ;

Mongin, F ;

Trécourt, F ;

Quéguiner, G ;

Marsais, F .

TETRAHEDRON LETTERS, 2004, 45 (42) :7873-7877

[2] Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling [J].

Bouillon, A ;

Lancelot, JC ;

Santos, JSD ;

Collot, V ;

Bovy, PR ;

Rault, S .

TETRAHEDRON, 2003, 59 (50) :10043-10049

[3] Synthesis of novel halopyridinylboronic acids and esters. Part 3: 2, or 3-halopyridin-4-yl-boronic acids and esters [J].

Bouillon, A ;

Lancelot, JC ;

Collot, V ;

Bovy, PR ;

Rault, S .

TETRAHEDRON, 2002, 58 (22) :4369-4373

[4] Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters [J].

Bouillon, A ;

Lancelot, JC ;

Collot, V ;

Bovy, PR ;

Rault, S .

TETRAHEDRON, 2002, 58 (17) :3323-3328

[5] Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters [J].

Bouillon, A ;

Lancelot, JC ;

Collot, V ;

Bovy, PR ;

Rault, S .

TETRAHEDRON, 2002, 58 (14) :2885-2890

[6] Chemistry of the organodiamides of magnesium, aluminum and mixed Mg-Al systems. A review of the heterocumulene reactivity on the Mg-Al centers [J].

Chang, CC ;

Ameerunisha, MS .

COORDINATION CHEMISTRY REVIEWS, 1999, 189 :199-278

[7] 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

[8]

CLARKE AJ, 1974, TETRAHEDRON LETT, P2373

[9]

Clayden J., 2002, ORGANOLITHIUMS SELEC

[10] LITHIATION OF METHOXYPYRIDINES DIRECTED BY ALPHA-AMINO ALKOXIDES [J].

COMINS, DL ;

KILLPACK, MO .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :69-73

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