Synthesis of functionalized nitroarylmagnesium halides via an iodine-magnesium exchange

被引：47

作者：

Sapountzis, L ^{[1
]}

Dube, H ^{[1
]}

Lewis, R ^{[1
]}

Gommermann, N ^{[1
]}

Knochel, P ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 07期

关键词：

D O I：

10.1021/jo048132o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40 degrees C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.

引用

页码：2445 / 2454

页数：10

共 79 条

[21] Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues [J].

Ghosez, L ;

Franc, C ;

Denonne, F ;

Cuisinier, C ;

Touillaux, R .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (11) :1827-1839

[22] A SIMPLE METHOD FOR TERT-BUTOXYCARBONYLATION OF AMIDES [J].

GREHN, L ;

GUNNARSSON, K ;

RAGNARSSON, U .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (09) :745-750

[23] THE TRIAZENE MOIETY AS A PROTECTING GROUP FOR AROMATIC-AMINES [J].

GROSS, ML ;

BLANK, DH ;

WELCH, WM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2104-2109

[24]

Hamdouchi C., 1996, Handbook of Grignard Reagents, Eds, P145

[25] ARYLBORONIC ACIDS .5. METHYL-SUBSTITUTED BORONIC ACIDS, BORINIC ACIDS AND TRIARYLBORONS [J].

HAWKINS, RT ;

LENNARZ, WJ ;

SNYDER, HR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (12) :3053-3059

[26]

Jensen AE, 2002, SYNTHESIS-STUTTGART, P565

[27]

Kitagawa K, 2000, ANGEW CHEM INT EDIT, V39, P2481, DOI 10.1002/1521-3773(20000717)39:14<2481::AID-ANIE2481>3.0.CO

[28]

2-J

[29]

KITAGAWA K, 2000, ANGEW CHEM, V112, P2594, DOI DOI 10.1002/1521-3757(20000717)112:14<2594::AID-ANGE2594>3.0.CO

[30]

2-O

← 1 2 3 4 5 6 7 8 →