First iron-catalyzed guanylation of amines: a simple and highly efficient protocol to guanidines

被引:34
作者
Pottabathula, Srinivas [1 ]
Royo, Beatriz [1 ]
机构
[1] Univ Nova Lisboa, Inst Tecnol Quim & Biol, EAN, P-2780157 Oeiras, Portugal
关键词
Iron catalyzed; Guanylation; Homogeneous catalysis; Amines; Guanidines; EARTH-METAL COMPLEXES; SUBSTITUTED GUANIDINES; ORGANIC-SYNTHESIS; SECONDARY-AMINES; N-H; CARBODIIMIDES; CONSTRUCTION; LANTHANIDE; ACTIVATION; YTTRIUM;
D O I
10.1016/j.tetlet.2012.07.065
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first iron-catalyzed guanylation of amines is reported. Commercially available Fe(OAc)(2) acts as an excellent catalyst for the addition of amines to carbodiimides. The reaction is broadly applicable to a variety of primary, secondary, and heterocyclic amines, and tolerates a wide range of functionalities allowing the easy preparation of a large family of guanidines. The low price and low toxicity of the commercially available iron catalyst make this methodology highly attractive. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5156 / 5158
页数:3
相关论文
共 31 条
  • [1] Simple, Versatile, and Efficient Catalysts for Guanylation of Amines
    Alonso-Moreno, Carlos
    Carrillo-Hermosilla, Fernando
    Garces, Andres
    Otero, Antonio
    Lopez-Solera, Isabel
    Rodriguez, Ana M.
    Antinolo, Antonio
    [J]. ORGANOMETALLICS, 2010, 29 (12) : 2789 - 2795
  • [2] The coordination chemistry of guanidines and guanidinates
    Bailey, PJ
    Pace, S
    [J]. COORDINATION CHEMISTRY REVIEWS, 2001, 214 : 91 - 141
  • [3] Searching for precursors to metal-metal bonded dipalladium species:: A study of Pd24+ complexes
    Berry, JF
    Cotton, FA
    Ibragimov, SA
    Murillo, CA
    Wang, XP
    [J]. INORGANIC CHEMISTRY, 2005, 44 (17) : 6129 - 6137
  • [4] Iron-catalyzed reactions in organic synthesis
    Bolm, C
    Legros, J
    Le Paih, J
    Zani, L
    [J]. CHEMICAL REVIEWS, 2004, 104 (12) : 6217 - 6254
  • [5] Activation of Carbodiimide and Transformation with Amine to Guanidinate Group by Ln(OAr)3(THF)2 (Ln: Lanthanide and Yttrium) and Ln(OAr)3(THF)2 as a Novel Precatalyst for Addition of Amines to Carbodiimides: Influence of Aryloxide Group
    Cao, Yang
    Du, Zhu
    Li, Wenbo
    Li, Junmei
    Zhang, Yong
    Xu, Fan
    Shen, Qi
    [J]. INORGANIC CHEMISTRY, 2011, 50 (08) : 3729 - 3737
  • [6] Unprecedented synthesis of iron-NHC complexes by C-H activation of imidazolium salts. Mild catalysts for reduction of sulfoxides
    Cardoso, Joao M. S.
    Royo, Beatriz
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (41) : 4944 - 4946
  • [7] Sustainable metal catalysis with iron: From rust to a rising star?
    Enthaler, Stephan
    Junge, Kathrin
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) : 3317 - 3321
  • [8] Guilman A., 1990, PHARMACOL BASIS THER, P899
  • [9] Guanidines in organic synthesis
    Ishikawa, T
    Kumamoto, T
    [J]. SYNTHESIS-STUTTGART, 2006, (05): : 737 - 752
  • [10] Ishikawa T, 2002, CHEM-EUR J, V8, P553, DOI 10.1002/1521-3765(20020201)8:3<552::AID-CHEM552>3.0.CO