Palladium-catalyzed homocoupling of arenediazonium salts: an operationally simple synthesis of symmetrical biaryls

被引:40
|
作者
Robinson, Monique K. [1 ]
Kochurina, Vasilina S. [1 ]
Hanna, James M., Jr. [1 ]
机构
[1] Winthrop Univ, Dept Phys Chem & Geol, Rock Hill, SC 29733 USA
关键词
arenediazonium salts; Symmetrical biaryls; palladiumcatalyzed; homocoupling;
D O I
10.1016/j.tetlet.2007.08.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple procedure for the intermolecular homocoupling of arenediazonium salts in air using a catalytic amount of palladium acetate is described. The optimum conditions were found to be 15 mol % palladium acetate in refluxing methanol, with no additional terminal reducing agent required. These optimized conditions were used to prepare biaryls from several arenediazonium tetrafluoroborate salts, and most examples proceeded in moderate to high yields. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7687 / 7690
页数:4
相关论文
共 50 条
  • [1] Pd(OAc)2 catalyzed homocoupling of arenediazonium salts in ionic liquids: synthesis of symmetrical biaryls
    Savanur, Hemantkumar M.
    Kalkhambkar, Rajesh G.
    Laali, Kenneth K.
    TETRAHEDRON LETTERS, 2016, 57 (06) : 663 - 667
  • [2] Synthesis of Symmetrical Biaryls through Palladium-Catalyzed Ligand-Free Homocoupling of Aryliodine(III) Diacetates
    Xiong, Qiheng
    Fu, Zhengjiang
    Li, Zhaojie
    Cai, Hu
    SYNLETT, 2015, 26 (07) : 975 - 979
  • [3] Ultrasound-Assisted Synthesis of Symmetrical Biaryls by Palladium-Catalyzed Homocoupling of Aryl n-Butyl Tellurides
    Singh, Fatehl Veer
    Stefani, Helio A.
    SYNLETT, 2008, (20) : 3221 - 3225
  • [4] Palladium-catalyzed hydroarylation of alkynes with arenediazonium salts
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    Persiani, Daniela
    ORGANIC LETTERS, 2008, 10 (08) : 1597 - 1600
  • [5] Palladium-Catalyzed Synthesis of Symmetrical Biaryls Under Microwave Irradiation and Conventional Heating
    Hajipour, Abdol Reza
    Rafiee, Fatemeh
    SYNTHETIC COMMUNICATIONS, 2013, 43 (09) : 1314 - 1327
  • [6] Palladium-Catalyzed Carbonylative Homocoupling of 2-Iodophenols for the Synthesis of Symmetrical Xanthones
    Lokolkar, Manjunath S.
    Bhanage, Bhalchandra M.
    SYNLETT, 2023, 34 (19) : 2329 - 2335
  • [7] CHED 269-Mechanistic investigation of the palladium-catalyzed homocoupling of arenediazonium salts: Insight from Hammett studies
    McClellan, Joshua L.
    Hanna, James M., Jr.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [8] CHED 571-Palladium-catalyzed homocoupling of arenediazonium salts: Scope and limitations
    Hanna, James M., Jr.
    Kochurina, Vasilina S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [9] Palladium-catalyzed homocoupling reaction of 1-iodoalkynes: A simple and efficient synthesis of symmetrical 1,3-diynes
    Damle, SV
    Seomoon, D
    Lee, PH
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18): : 7085 - 7087
  • [10] The palladium-catalyzed Heck arylation of olefins with arenediazonium salts as a sustainable strategy in organic synthesis
    Oliveira, Caio C.
    Correia, Carlos Roque D.
    CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, 2020, 26