Iron-catalyzed annulation reaction of arylindium reagents and alkynes to produce substituted naphthalenes

被引:38
作者
Adak, Laksmikanta [1 ]
Yoshikai, Naohiko [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
基金
新加坡国家研究基金会;
关键词
Iron catalysis; Organoindium reagent; Alkyne; C-H bond functionalization; Naphthalene; H BOND ACTIVATION; C-H; INTERNAL ALKYNES; ARYL IODIDES; COUPLING REACTIONS; METAL; INDIUM; ARYLMAGNESIATION; CARBOMETALATION; PHENYLAZOLES;
D O I
10.1016/j.tet.2012.04.004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report here an iron-bisphosphine complex-catalyzed annulation reaction of an arylindium reagent and two alkyne molecules that affords a substituted naphthalene derivative in moderate to good yield. The reaction represents a new example of iron-catalyzed C-C bond forming reactions via C-H bond functionalization. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5167 / 5171
页数:5
相关论文
共 57 条
  • [1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [2] Cobalt-Catalyzed Preparation of Arylindium Reagents from Aryl and Heteroaryl Bromides
    Adak, Laksmikanta
    Yoshikai, Naohiko
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18) : 7563 - 7568
  • [3] The larger acenes: Versatile organic semiconductors
    Anthony, John E.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) : 452 - 483
  • [4] Araki S., 2007, Comprehensive Organometallic Chemistry III, V9, P649, DOI DOI 10.1016/B0-08-045047-4/00122-9
  • [5] Recent advances in indium-promoted organic reactions
    Auge, Jacques
    Lubin-Germain, Nadege
    Uziel, Jacques
    [J]. SYNTHESIS-STUTTGART, 2007, (12): : 1739 - 1764
  • [6] Iron-catalysed Negishi coupling of benzyl halides and phosphates
    Bedford, Robin B.
    Huwe, Michael
    Wilkinson, Mark C.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (05) : 600 - 602
  • [7] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
  • [8] Preparation of aryl and heteroaryl indium(III) reagents by the direct insertion of indium in the presence of LiCl
    Chen, Yi-Hung
    Knochel, Paid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (40) : 7648 - 7651
  • [9] C-F and C-H Bond Activation of Fluorobenzenes and Fluoropyridines at Transition Metal Centers: How Fluorine Tips the Scales
    Clot, Eric
    Eisenstein, Odile
    Jasim, Naseralla
    Macgregor, Stuart A.
    Mcgrady, John E.
    Perutz, Robin N.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (05) : 333 - 348
  • [10] Exceptional Sensitivity of Metal-Aryl Bond Energies to ortho-Fluorine Substituents: Influence of the Metal, the Coordination Sphere, and the Spectator Ligands on M-C/H-C Bond Energy Correlations
    Clot, Eric
    Megret, Claire
    Eisenstein, Odile
    Perutz, Robin N.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) : 7817 - 7827