Decarboxylative functionalization of cinnamic acids

被引：106

作者：

Borah, Arun Jyoti ^{[1
]}

Yan, Guobing ^{[1
]}

机构：

[1] Lishui Univ, Dept Chem, Lishui City 323000, Zhejiang, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 30期

关键词：

ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; CROSS-COUPLING REACTION; COPPER-CATALYZED TRIFLUOROMETHYLATION; NITRO-HUNSDIECKER REACTION; BIOLOGICAL EVALUATION; BIARYL SYNTHESIS; OXIDATIVE DECARBOXYLATION; STEREOSELECTIVE-SYNTHESIS; AROMATIC-COMPOUNDS; ELEMENTAL SULFUR;

D O I：

10.1039/c5ob00727e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Decarboxylative functionalization of alpha, beta-unsaturated carboxylic acids is an emerging area that has been developed significantly in recent years. This critical review focuses on the different decarboxylative functionalization reactions of cinnamic acids leading to the formation of various C-C and C-heteroatom bonds. Apart from metal carboxylates, decarboxylation in cinnamic acids has been achieved efficiently under metal-free conditions, particularly via the use of hypervalent iodine reagents. We believe this review will encourage organic chemists to develop vinylic decarboxylation in a more appealing way with an understanding of new mechanistic insight.

引用

页码：8094 / 8115

页数：22

共 162 条

[1] Synthesis of diethyl 2-(aryl) vinylphosphonates by the Heck reaction catalysed by well-defined palladium complexes [J].

Al-Maksoud, Walid ;

Mesnager, Julien ;

Jaber, Farouk ;

Pinel, Catherine ;

Djakovitch, Laurent .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (20) :3222-3231

[2] SILVER(I)-CATALYZED OXIDATIVE DECARBOXYLATION OF ACIDS BY PEROXYDISULFATE - ROLE OF SILVER(II) [J].

ANDERSON, JM ;

KOCHI, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1651-&

[3] SILVER(II) COMPLEXES IN OXIDATIVE DECARBOXYLATION OF ACIDS [J].

ANDERSON, JM ;

KOCHI, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (04) :986-&

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

Baudoin, Olivier .

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

[5] 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

[6] 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

[7] Thionations Using a P4S10-Pyridine Complex in Solvents Such as Acetonitrile and Dimethyl Sulfone [J].

Bergman, Jan ;

Pettersson, Birgitta ;

Hasimbegovic, Vedran ;

Svensson, Per H. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) :1546-1553

[8] Decarboxylative Etherification of Aromatic Carboxylic Acids [J].

Bhadra, Sukalyan ;

Dzik, Wojciech I. ;

Goossen, Lukas J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) :9938-9941

[9] Design, synthesis and biological evaluation of peptidyl-vinylaminophosphonates as novel cysteine protease inhibitors [J].

Bhattacharya, Asish K. ;

Rana, Kalpeshkumar C. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (23) :7129-7135

[10] Anion-functionalized ionic liquids enhance the CuI-Catalyzed cross-coupling reaction of sulfinic acid salts with aryl halides and vinyl bromides [J].

Bian, Ming ;

Xu, Fada ;

Ma, Cheng .

SYNTHESIS-STUTTGART, 2007, (19) :2951-2956

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