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

被引:1267
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
  • [21] Biermann U, 2000, ANGEW CHEM INT EDIT, V39, P2206, DOI 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO
  • [22] 2-P
  • [23] Biermann U, 2000, ANGEW CHEM, V112, P2292
  • [24] Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides
    Bilodeau, Francois
    Brochu, Marie-Christine
    Guimond, Nicolas
    Thesen, Kris H.
    Forgione, Pat
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) : 1550 - 1560
  • [25] Breitmaier E., 1982, ORGANISCHE CHEMIE, P194
  • [26] ORGANOCOPPER INTERMIDIATES VIA DECARBOXYLATION OF CUPROUS CARBOXYLATES
    CAIRNCROSS, A
    ROLAND, JR
    HENDERSON, RM
    SHEPPARD, WA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) : 3187 - +
  • [27] Cairncross A., 1968, J. Am. Chem. Soc, V90, P2186
  • [28] Addition of alpha beta-unsaturated alcohols to the active methylene group Part I The action of ethyl acetoacetate on linalool and geraniol
    Carroll, MF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1940, : 704 - 706
  • [29] Chemical Synthesis with Inductively Heated Copper Flow Reactors
    Ceylan, Sascha
    Klande, Tobias
    Vogt, Carla
    Friese, Carsten
    Kirschning, Andreas
    [J]. SYNLETT, 2010, (13) : 2009 - 2013
  • [30] Two methods for direct ortho-arylation of benzoic acids
    Chiong, Hendrich A.
    Pham, Quynh-Nhu
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) : 9879 - 9884