A general method for meta and para functionalization of arenes using TMP2Mg•2LiCl

被引：116

作者：

Rohbogner, Christoph J. ^{[1
]}

Clososki, Giuliano C. ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 08期

关键词：

arenes; directed metalation; Grignard reagents; magnesium bisamides; phosphorodiamidates;

D O I：

10.1002/anie.200703382

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Getting directions: The (Me 2N)2P(O)O substituent serves as an effective directing-metalation group in the magnesiation of substituted arenes with TMP2Mg·2 LiCl (see scheme). This reaction can be used to achieve difficult substitution patterens by meta,para or para,meta functionalization. TMP = 2,2,6,6-tetramethylpiperamidyl, NEP = N-ethylpyrrolidone. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1503 / 1507

页数：5

共 67 条

[1] Palladium-catalyzed amination of aryl nonaflates [J].

Anderson, KW ;

Mendez-Perez, M ;

Priego, J ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25) :9563-9573

[2] Selective meta-deprotonation of toluene by using alkali-metal-mediated magnesiation [J].

Andrikopoulos, PC ;

Armstrong, DR ;

Graham, DV ;

Hevia, E ;

Kennedy, AR ;

Mulvey, RE ;

O'Hara, CT ;

Talmard, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3459-3462

[3]

ANDRIKOPOULOS PC, 2005, ANGEW CHEM, V117, P3525

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], 2004, ANGEW CHEM, V116, P5424

[6] Directed meta-metalation using alkali-metal-mediated zincation [J].

Armstrong, David R. ;

Clegg, William ;

Dale, Sophie H. ;

Hevia, Eva ;

Hogg, Lorna M. ;

Honeyman, Gordon W. ;

Mulvey, Robert E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3775-3778

[7] 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

[8]

Clayden J., 2002, ORGANOLITHIUMS SELEC

[9]

Clososki G. C., 2007, ANGEW CHEM, V119, P7825

[10] Direct magnesiation of polyfunctionalized arenes and heteroarenes using (tmp)2Mg-2LiCl [J].

Clososki, Giuliano C. ;

Rohbogner, Christoph J. ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7681-7684

← 1 2 3 4 5 6 7 →