Pre-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide

被引：76

作者：

Clegg, W

Dale, SH

Hevia, E

Honeyman, GW

Mulvey, RE

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, WestCHEM, Glasgow G1 1XL, Lanark, Scotland

[2] Univ Newcastle Upon Tyne, Sch Nat Sci Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 15期

关键词：

alkali metals; amides; complex-induced proximity effect; metalation; zinc;

D O I：

10.1002/anie.200503202

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Catch me if you can: Invisible using standard electrophilic substitution detection methods, two distinct ortho-metalated "intermediates" generated by alkali-metal-mediated zincation of N,N-diisopropylbenzamide are structurally elucidated. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：2370 / 2374

页数：5

相关论文

共 24 条

[1] DIPOLE-STABILIZED CARBANIONS - EVIDENCE FOR A COMPLEX IN THE ALPHA'-LITHIATION OF N,N-DIMETHYL-2,4,6-TRIISOPROPYLBENZAMIDE [J].

ALASEER, M ;

BEAK, P ;

HAY, D ;

KEMPF, DJ ;

MILLS, S ;

SMITH, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2080-2082

[2] Sodium dialkyl-amidozincates: Alkyl or amido bases? An experimental and theoretical case study [J].

Andrikopoulos, PC ;

Armstrong, DR ;

Barley, HRL ;

Clegg, W ;

Dale, SH ;

Hevia, E ;

Honeyman, GW ;

Kennedy, AR ;

Mulvey, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6184-6185

[3]

[Anonymous], 2004, METAL CATALYZED CROS

[4]

Armstrong D. R., 2004, Angew. Chem., V116, P2187

[5] Controlling chemoselectivity in the lithiation of substituted aromatic tertiary amides [J].

Armstrong, DR ;

Boss, SR ;

Clayden, J ;

Haigh, R ;

Kirmani, BA ;

Linton, DJ ;

Schooler, P ;

Wheatley, AEH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (16) :2135-2138

[6] Variations in the solid-state, solution and theoretical structures of a laterally deprotonated aromatic tertiary amide [J].

Armstrong, DR ;

Clayden, J ;

Haigh, R ;

Linton, DJ ;

Schooler, P ;

Wheatley, AEH .

CHEMICAL COMMUNICATIONS, 2003, (14) :1694-1695

[7] Alkali-metal-mediated zineation of ferrocene: Synthesis, structure, and reactivity of a lithium tmp/zincate reagent [J].

Barley, HRL ;

Clegg, W ;

Dale, SH ;

Hevia, E ;

Honeyman, GW ;

Kennedy, AR ;

Mulvey, RE .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (37) :6018-6021

[8]

BARLEY HRL, 2005, ANGEW CHEM, V117, P6172

[9] DOMINANCE OF THE PROXIMITY EFFECT OF COMPLEXATION OVER RESONANCE AND INDUCTIVE EFFECTS IN DIRECTING A METALATION - REGIOSPECIFIC BETA-LITHIATION OF N,N-DIISOPROPYLCYCLOHEX-3-ENECARBOXAMIDE AND OF N,N-DIISOPROPYL-2-METHYLPENT-4-ENECARBOXAMIDE [J].

BEAK, P ;

HUNTER, JE ;

JUN, YM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (20) :6350-6351

[10] 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