Synthesis of Vinylsulfones Via Palladium-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts

被引：39

作者：

Guo, Ruqing ^{[1
]}

Gui, Qingwen ^{[1
]}

Wang, Dadian ^{[1
]}

Tan, Ze ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

来源：

CATALYSIS LETTERS | 2014年 / 144卷 / 08期

基金：

中国国家自然科学基金;

关键词：

Pd(AcO)(2); Ag2CO3; Cinnamic acid; Aromatic sulfinic acid sodium salts; Decarboxylative coupling; ALPHA-OXOCARBOXYLIC ACIDS; C-H; DESULFITATIVE ARYLATION; CARBOXYLIC-ACIDS; ARYL BROMIDES; VERSATILE CATALYST; BIARYL SYNTHESIS; BENZOIC-ACIDS; OLEFINATION; ACYLATION;

D O I：

10.1007/s10562-014-1286-5

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A highly efficient synthesis of vinylsulfones was achieved via decarboxylative cross-coupling reaction of cinnamic acids with aromatic sulfinic acid sodium salts catalyzed by Pd(OAc)(2) and dppb in the presence of Ag2CO3. The reaction was found to furnish various vinylsulfones in good yields instead of the expected desulfitative product stilbenes. Mechanistic investigation also suggested that the decarboxylation is likely to take place after the transmetallation step.

引用

页码：1377 / 1383

页数：7

共 65 条

[1] Validation of lanthanide chiral shift reagents for determination of absolute configuration: Total synthesis of glisoprenin A [J].

Adams, CM ;

Ghosh, I ;

Kishi, Y .

ORGANIC LETTERS, 2004, 6 (25) :4723-4726

[2]

[Anonymous], 2011, ANGEW CHEM INT EDIT

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

Baudoin, Olivier .

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

[4] 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

[5] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction [J].

Becht, Jean-Michel ;

Catala, Cedric ;

Le Drian, Claude ;

Wagner, Alain .

ORGANIC LETTERS, 2007, 9 (09) :1781-1783

[6]

Biswanath D, 2011, SYNTHESIS-STUTTGART, V18, P2941

[7] The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates [J].

Chen, Jianbin ;

Sun, Yang ;

Liu, Bin ;

Liu, Dongfang ;

Cheng, Jiang .

CHEMICAL COMMUNICATIONS, 2012, 48 (03) :449-451

[8] Decarboxylative homocoupling of (hetero) aromatic carboxylic acids [J].

Cornella, Josep ;

Lahlali, Hicham ;

Larrosa, Igor .

CHEMICAL COMMUNICATIONS, 2010, 46 (43) :8276-8278

[9] 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

[10] Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids [J].

Fang, Ping ;

Li, Mingzong ;

Ge, Haibo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) :11898-11899

← 1 2 3 4 5 6 7 →