Experimental and theoretical study on the cyclic(alkyl)(amino)carbene-copper catalyzed Friedel-Crafts reaction ofN,N-dialkylanilines with styrenes

被引:9
作者
Ma, Wentao [1 ]
Zhai, Gaowen [1 ]
Hu, Xingbang [1 ]
Wu, Youting [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Separat Engn Res Ctr, Nanjing 210093, Peoples R China
基金
中国国家自然科学基金;
关键词
CYCLIC (ALKYL)(AMINO)CARBENES; AROMATIC-AMINES; ARYL BROMIDES; GOLD; COMPLEXES; COPPER; ALKYLATION; HYDROARYLATION; CARBOXYLATION; AMINATION;
D O I
10.1039/c9ob02734c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Friedel-Crafts reaction of alkalinous substrates is challenging because of the coordination between amines and traditional acid catalysts. Based on theoretical research, we designed a catalytic process for the Friedel-Crafts reactions ofN,N-dialkylanilines in the presence of CAAC-CuCl [CAAC = cyclic(alkyl)(amino)carbene] and KB(C6F5)(4). Experimental results show that the catalytic system is suitable for a series ofN,N-dialkylanilines and styrenes with good to excellent yields ofpara-selectivity products. The results are comparable to those obtained in carbene-gold catalyzed processes.
引用
收藏
页码:4272 / 4275
页数:4
相关论文
共 47 条
  • [11] Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity
    Dorel, Ruth
    Echavarren, Antonio M.
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9028 - 9072
  • [12] Gas-phase synthesis and reactivity of a gold carbene complex
    Fedorov, Alexey
    Moret, Marc-Etienne
    Chen, Peter
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) : 8880 - +
  • [13] Potential Energy Surface for (Retro-)Cyclopropanation: Metathesis with a Cationic Gold Complex
    Fedorov, Alexey
    Batiste, Laurent
    Bach, Andreas
    Birney, David M.
    Chen, Peter
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) : 12162 - 12171
  • [14] Preparation, structure, and reactivity of nonstabilized organoiron compounds.: Implications for iron-catalyzed cross coupling reactions
    Fuerstner, Alois
    Martin, Ruben
    Krause, Helga
    Seidel, Guenter
    Goddard, Richard
    Lehmann, Christian W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8773 - 8787
  • [15] Catalytic enantioselective Friedel-Crafts reactions of aromatic compounds with glyoxylate: A simple procedure for the synthesis of optically active aromatic mandelic acid esters
    Gathergood, N
    Zhuang, W
    Jorgensen, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) : 12517 - 12522
  • [16] Giannerini M, 2013, NAT CHEM, V5, P667, DOI [10.1038/NCHEM.1678, 10.1038/nchem.1678]
  • [17] Copper Salts as Additives in Gold(I)-Catalyzed Reactions
    Guerinot, Amandine
    Fang, Weizhen
    Sircoglou, Marie
    Bour, Christophe
    Bezzenine-Lafollee, Sophie
    Gandon, Vincent
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) : 5848 - 5852
  • [18] 9-Borabicyclo[3.3.l]nonane-induced Friedel-Crafts benzylation of arenes with benzyl fluorides
    Guo, Jing
    Bamford, Karlee L.
    Stephan, Douglas W.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (21) : 5258 - 5261
  • [19] Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast CrossCoupling of Organolithium Reagents
    Heijnen, Dorus
    Tosi, Filippo
    Vila, Carlos
    Stuart, Marc C. A.
    Elsinga, Philip H.
    Szymanski, Wiktor
    Feringa, Ben L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) : 3354 - 3359
  • [20] Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility
    Hu, Feng
    Patel, Mehulkumar
    Luo, Feixiang
    Flach, Carol
    Mendelsohn, Richard
    Garfunkel, Eric
    He, Huixin
    Szostak, Michal
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (45) : 14473 - 14480