Aldehydes and Ketones Formation: Copper-Catalyzed Aerobic Oxidative Decarboxylation of Phenylacetic Acids and α-Hydroxyphenylacetic Acids

被引:105
作者
Feng, Qiang [1 ]
Song, Qiuling [1 ]
机构
[1] Huaqiao Univ, Coll Chem Engn, Inst Next Generat Matter Transformat, Xiamen 361021, Fujian, Peoples R China
基金
美国国家科学基金会;
关键词
HETEROAROMATIC CARBOXYLIC-ACIDS; CROSS-COUPLING REACTION; ARYL HALIDES; BOND-CLEAVAGE; ALCOHOLS; PD; NANOPARTICLES; OLEFINATION;
D O I
10.1021/jo402778p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aromatic aldehydes or ketones from copper catalyzed aerobic oxidative decarboxylation of phenylacetic acids and alpha-hydroxyphenylacetic acids have been synthesized. This reaction combined decarboxylation, dioxygen activation, and C-H bond oxidation steps in a one-pot protocol with molecular oxygen as the sole terminal oxidant. This reaction represents a novel decarboxylation of an sp(3)-hybridized carbon and the use of a benzylic carboxylic acid as a source of carbonyl compounds.
引用
收藏
页码:1867 / 1871
页数:5
相关论文
共 40 条
  • [1] Safe Use of a Toxic Compound: Heterogeneous OsO4 Catalysis in a Nanobrush Polymer Microreactor
    Basavaraju, K. C.
    Sharma, Siddharth
    Maurya, Ram Awatar
    Kim, Dong-Pyo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (26) : 6735 - 6738
  • [2] 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
  • [3] THE ORGANOMETALLIC CHEMISTRY OF ALKANES
    CRABTREE, RH
    [J]. CHEMICAL REVIEWS, 1985, 85 (04) : 245 - 269
  • [4] Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways
    Dzik, Wojciech I.
    Lange, Paul P.
    Goossen, Lukas J.
    [J]. CHEMICAL SCIENCE, 2012, 3 (09) : 2671 - 2678
  • [5] Copper-Catalyzed Decarboxylative CN Triple Bond Formation: Direct Synthesis of Benzonitriles from Phenylacetic Acids Under O2 Atmosphere
    Feng, Qiang
    Song, Qiuling
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (08) : 1697 - 1702
  • [6] Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners
    Forgione, Pat
    Brochu, Marie-Christine
    St-Onge, Miguel
    Thesen, Kris H.
    Bailey, Murray D.
    Bilodeau, Francois
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) : 11350 - 11351
  • [7] Corboxylic acids as substrates in homogeneous catalysts
    Goossen, Lukas J.
    Rodriguez, Nuria
    Goossen, Kathe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) : 3100 - 3120
  • [8] Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides
    Goossen, Lukas J.
    Rodriguez, Nuria
    Melzer, Bettina
    Linder, Christophe
    Deng, Guojun
    Levy, Laura M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) : 4824 - 4833
  • [9] Highly selective, economical and efficient oxidation of alcohols to aldehydes and ketones by air and sunlight or visible light in the presence of porphyrins sensitizers
    Hajimohammadi, Mahdi
    Safari, Nasser
    Mofakham, Hamid
    Deyhimi, Farzad
    [J]. GREEN CHEMISTRY, 2011, 13 (04) : 991 - 997
  • [10] Transition metal-catalyzed carbon-carbon bond activation
    Jun, CH
    [J]. CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) : 610 - 618