Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids

被引：315

作者：

Fang, Ping ^{[1
]}

Li, Mingzong ^{[1
]}

Ge, Haibo ^{[1
]}

机构：

[1] Indiana Univ Purdue Univ, Dept Chem & Biol Chem, Indianapolis, IN 46202 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 34期

关键词：

BENZOPHENONE RELATED-COMPOUNDS; CARBOXYLIC-ACIDS; BIARYL SYNTHESIS; AROMATIC CARBOXYLATES; DIRECT ARYLATION; BENZOIC-ACIDS; ARYL BROMIDES; DERIVATIVES; PALLADATION; OLEFINATION;

D O I：

10.1021/ja105245f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel Pd-catalyzed decarboxylative ortho-acylation of acetanilides with alpha-oxocarboxylic acids is realized at room temperature. This reaction provides efficient access to o-acyl acetanilides under mild conditions.

引用

页码：11898 / 11899

页数：2

共 41 条

[1] New approaches for decarboxylative biaryl coupling [J].

Baudoin, Olivier .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1373-1375

[2] Biaryl synthesis via decarboxylative Pd-catalyzed reactions of arenecarboxylic acids and diaryliodonium triflates [J].

Becht, Jean-Michel ;

Le Drian, Claude .

ORGANIC LETTERS, 2008, 10 (14) :3161-3164

[3] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[4] Intermolecular Decarboxylative Direct C-3 Arylation of Indoles with Benzoic Acids [J].

Cornella, Josep ;

Lu, Pengfei ;

Larrosa, Igor .

ORGANIC LETTERS, 2009, 11 (23) :5506-5509

[5] HOMOLYTIC ACYLATION OF PROTONATED PYRIDINES AND PYRAZINES WITH ALPHA-KETO ACIDS - THE PROBLEM OF MONOACYLATION [J].

FONTANA, F ;

MINISCI, F ;

BARBOSA, MCN ;

VISMARA, E .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2866-2869

[6] Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners [J].

Forgione, Pat ;

Brochu, Marie-Christine ;

St-Onge, Miguel ;

Thesen, Kris H. ;

Bailey, Murray D. ;

Bilodeau, Francois .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) :11350-11351

[7] Palladium/copper-catalyzed decarboxylative cross-coupling of aryl chlorides with potassium carboxylates [J].

Goossen, Lukas J. ;

Zimmermann, Bettina ;

Knauber, Thomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) :7103-7106

[8] SYNTHESIS OF 2-SUBSTITUTED BIARYLS VIA Cu/Pd-CATALYZED DECARBOXYLATIVE CROSS-COUPLING OF 2-SUBSTITUTED POTASSIUM BENZOATES: 4-METHYL-2 '-NITROBIPHENYL AND 2-ACETYL-4 '-METHYLBIPHENYL [Biphenyl, 4-Methyl-2 '-nitro-] [Biphenyl, 4-Methyl-2 '-acetyl-] [J].

Goossen, Lukas J. ;

Rodirguez, Nuria ;

Linder, Christophe ;

Zimmermann, Bettina ;

Knauber, Thomas .

ORGANIC SYNTHESES, 2008, 85 :196-+

[9] New catalytic transformations of carboxylic acids [J].

Goossen, Lukas J. ;

Goossen, Kaethe ;

Rodriguez, Nuria ;

Blanchot, Mathieu ;

Linder, Christophe ;

Zimmermann, Bettina .

PURE AND APPLIED CHEMISTRY, 2008, 80 (08) :1725-1733

[10] Synthesis of ketones from α-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling [J].

Goossen, Lukas J. ;

Rudolphi, Felix ;

Oppel, Christoph ;

Rodriguez, Nuria .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3043-3045

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