Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides

被引：27
|
作者：
Haley, Christopher K. [1 ]
Gilmore, Christopher D. [1 ]
Stoltz, Brian M. [1 ]
机构：
[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
TETRAHEDRON | 2013年 / 69卷 / 27-28期
关键词：
Decarboxylative cross-coupling; (2-Azaaryl)carboxylates; Palladium; Copper; DIRECT ARYLATION; AZINE; ARENE; ACIDS; SCOPE; MILD; AIR;
D O I：
10.1016/j.tet.2013.03.085
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic method for the decarboxylative coupling of 2-(azaaryl)carboxylates with aryl halides is described. The decarboxylative cross-coupling presented is mediated by a system catalytic in both palladium and copper without requiring stoichiometric amounts of organometallic reagents or organoboronic acids. This method circumvents additional synthetic steps required to prepare 2-azaatyl organometallics and organoborates as nucleophilic coupling partners, which are prone to protodemetallation and protodeborylation and produce potentially toxic byproducts. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5732 / 5736
页数：5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Decarboxylative Couplings of 2-(2-Azaaryl)acetates with Aryl Halides and Triflates
    Shang, Rui
    Yang, Zhi-Wei
    Wang, Yan
    Zhang, Song-Lin
    Liu, Lei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) : 14391 - 14393
  • [2] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    JIANG YuanYe FU Yao LIU Lei Department of Chemistry University of Science and Technology of China Hefei China Department of Chemistry Tsinghua University Beijing China
    Science China(Chemistry), 2012, 55 (10) : 2057 - 2062
  • [3] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    JIANG YuanYeFU Yao LIU Lei Department of ChemistryUniversity of Science and Technology of ChinaHefei China Department of ChemistryTsinghua UniversityBeijing China
    中国科学:化学, 2012, 42 (10) : 1493 - 1493
  • [4] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    JIANG YuanYe
    Science China(Chemistry), 2012, (10) : 2057 - 2062
  • [5] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    YuanYe Jiang
    Yao Fu
    Lei Liu
    Science China Chemistry, 2012, 55 : 2057 - 2062
  • [6] Mechanism of palladium-catalyzed decarboxylative cross-coupling between cyanoacetate salts and aryl halides
    Jiang YuanYe
    Fu Yao
    Liu Lei
    SCIENCE CHINA-CHEMISTRY, 2012, 55 (10) : 2057 - 2062
  • [7] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
    Schmink, Jason R.
    Krska, Shane W.
    Tudge, Matthew T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [8] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
    ALHASSAN, MI
    SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
  • [9] 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
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05): : 1550 - 1560
  • [10] Palladium-Catalyzed Carbonylative Coupling of (2-Azaaryl) methyl Anion Equivalents with (Hetero)Aryl Bromides
    Jusseau, Xavier
    Yin, Hongfei
    Lindhardt, Anders T.
    Skrydstrup, Troels
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (48) : 15785 - 15789
12345