Transition metal-catalyzed decarboxylative cross-coupling reactions

被引:436
作者
Shang Rui [1 ]
Liu Lei [1 ,2 ]
机构
[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
decarboxylation; cross-coupling reaction; transition metal; catalysis; organic synthesis; CARBOXYLIC-ACIDS; BIARYL SYNTHESIS; BENZOIC-ACIDS; ARENECARBOXYLIC ACIDS; ARYL HALIDES; C-H; AROMATIC CARBOXYLATES; VERSATILE CATALYST; DIRECT ARYLATION; OLEFINATION;
D O I
10.1007/s11426-011-4381-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transition metal-catalyzed decarboxylative cross-coupling reactions have recently emerged as a new and important category of organic transformations that find versatile applications in the construction of carbon-carbon and carbon-heteroatom bonds. The use of relatively cheap and stable carboxylic acids to replace organometallic reagents enables the decarboxylative cross-coupling reactions to proceed with good selectivities and functional group tolerance. In the present review we summarize the various types of decarboxylative cross-coupling reactions catalyzed by different transition metal complexes. The scope and applications of these reactions are described. The challenges and opportunities in the field are discussed.
引用
收藏
页码:1670 / 1687
页数:18
相关论文
共 83 条
[1]   3,4-Propylenedioxypyrrole-Based Conjugated Oligomers via Pd-Mediated Decarboxylative Cross Coupling [J].
Arroyave, Frank A. ;
Reynolds, John R. .
ORGANIC LETTERS, 2010, 12 (06) :1328-1331
[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]   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
[4]   Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3-Csp) of Natural α-Amino Acids and Alkynes [J].
Bi, Hai-Peng ;
Teng, Qingfeng ;
Guan, Min ;
Chen, Wen-Wen ;
Liang, Yong-Min ;
Yao, Xiaojun ;
Li, Chao-Jun .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :783-788
[5]   The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].
Bi, Hai-Peng ;
Zhao, Liang ;
Liang, Yong-Min ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795
[6]   DECARBOXYLATIVE COUPLINGS OF 2,6-DINITROBENZOIC ACID [J].
BJORKLUN.C ;
NILSSON, M .
ACTA CHEMICA SCANDINAVICA, 1968, 22 (08) :2585-&
[7]   ORGANOCOPPER INTERMIDIATES VIA DECARBOXYLATION OF CUPROUS CARBOXYLATES [J].
CAIRNCROSS, A ;
ROLAND, JR ;
HENDERSON, RM ;
SHEPPARD, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3187-+
[8]   COPPER-QUINOLINE DECARBOXYLATION [J].
COHEN, T ;
SCHAMBACH, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3189-+
[9]   A Novel Mode of Reactivity for Gold(I): The Decarboxylative Activation of (Hetero) Aromatic Carboxylic Acids [J].
Cornella, Josep ;
Rosillo-Lopez, Martin ;
Larrosa, Igor .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1359-1366
[10]   Decarboxylative homocoupling of (hetero) aromatic carboxylic acids [J].
Cornella, Josep ;
Lahlali, Hicham ;
Larrosa, Igor .
CHEMICAL COMMUNICATIONS, 2010, 46 (43) :8276-8278