Decarboxylative coupling reactions: a modern strategy for C-C-bond formation

被引:1297
作者
Rodriguez, Nuria [1 ]
Goossen, Lukas J. [1 ]
机构
[1] TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany
关键词
AROMATIC CARBOXYLIC-ACIDS; PALLADIUM-CATALYZED DECARBOXYLATION; AB-INITIO PSEUDOPOTENTIALS; ALPHA-OXOCARBOXYLIC ACIDS; SUBSTITUTED BENZOIC-ACIDS; ACTIVATED IN-SITU; ARYL HALIDES; OXIDATIVE DECARBOXYLATION; BIARYL SYNTHESIS; ARENECARBOXYLIC ACIDS;
D O I
10.1039/c1cs15093f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This critical review examines transition metal-catalyzed decarboxylative couplings that have emerged within recent years as a powerful strategy to form carbon-carbon or carbon-heteroatom bonds starting from carboxylic acids. In these reactions, C-C bonds to carboxylate groups are cleaved, and in their place, new carbon-carbon bonds are formed. Decarboxylative cross-couplings constitute advantageous alternatives to traditional cross-coupling or addition reactions involving preformed organometallic reagents. Decarboxylative reaction variants are also known for Heck reactions, direct arylation processes, and carbon-heteroatom bond forming reactions.
引用
收藏
页码:5030 / 5048
页数:19
相关论文
共 183 条
[31]   Mechanisms of decarboxylation of ortho-substituted benzoic acids [J].
Chuchev, Krum ;
BelBruno, Joseph J. .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2007, 807 (1-3) :1-9
[32]   COPPER-QUINOLINE DECARBOXYLATION [J].
COHEN, T ;
SCHAMBACH, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3189-+
[33]   PRODUCTS AND KINETICS OF DECARBOXYLATION OF ACTIVATED AND UNACTIVATED AROMATIC CUPROUS CARBOXYLATES IN PYRIDINE AND IN QUINOLINE [J].
COHEN, T ;
BERNINGER, RW ;
WOOD, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (05) :837-848
[34]   Decarboxylative homocoupling of (hetero) aromatic carboxylic acids [J].
Cornella, Josep ;
Lahlali, Hicham ;
Larrosa, Igor .
CHEMICAL COMMUNICATIONS, 2010, 46 (43) :8276-8278
[35]   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
[36]   Silver-catalysed protodecarboxylation of ortho-substituted benzoic acids [J].
Cornella, Josep ;
Sanchez, Carolina ;
Banawa, David ;
Larrosa, Igor .
CHEMICAL COMMUNICATIONS, 2009, (46) :7176-7178
[37]   Physical properties and chemical constitution part V Alkyl ketones [J].
Cowan, DM ;
Jeffery, GH ;
Vogel, AI .
JOURNAL OF THE CHEMICAL SOCIETY, 1940, :171-176
[38]   THE EVOLUTION OF CARBOXYLATE SPECIES IN THE FRAMEWORK OF CO-H-2 SYNTHESIS - REDUCTION OF ACETIC-ACID ON THE CO,CU,FE SYSTEM [J].
CRESSELY, J ;
FARKHANI, D ;
DELUZARCHE, A ;
KIENNEMANN, A .
MATERIALS CHEMISTRY AND PHYSICS, 1984, 11 (05) :413-431
[39]   Pd-catalysed decarboxylative Suzuki reactions and orthogonal Cu-based O-arylation of aromatic carboxylic acids [J].
Dai, Jian-Jun ;
Liu, Jing-Hui ;
Luo, Dong-Fen ;
Liu, Lei .
CHEMICAL COMMUNICATIONS, 2011, 47 (02) :677-679
[40]   Development of a catalytic aromatic decarboxylation reaction [J].
Dickstein, Joshua S. ;
Mulrooney, Carol A. ;
O'Brien, Erin M. ;
Morgan, Barbara J. ;
Kozlowski, Marisa C. .
ORGANIC LETTERS, 2007, 9 (13) :2441-2444