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

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 38期

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

页码：5156 / 5158

页数：3

共 31 条

[1] Simple, Versatile, and Efficient Catalysts for Guanylation of Amines [J].

Alonso-Moreno, Carlos ;

Carrillo-Hermosilla, Fernando ;

Garces, Andres ;

Otero, Antonio ;

Lopez-Solera, Isabel ;

Rodriguez, Ana M. ;

Antinolo, Antonio .

ORGANOMETALLICS, 2010, 29 (12) :2789-2795

[2] The coordination chemistry of guanidines and guanidinates [J].

Bailey, PJ ;

Pace, S .

COORDINATION CHEMISTRY REVIEWS, 2001, 214 :91-141

[3] Searching for precursors to metal-metal bonded dipalladium species:: A study of Pd24+ complexes [J].

Berry, JF ;

Cotton, FA ;

Ibragimov, SA ;

Murillo, CA ;

Wang, XP .

INORGANIC CHEMISTRY, 2005, 44 (17) :6129-6137

[4] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

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 [J].

Cao, Yang ;

Du, Zhu ;

Li, Wenbo ;

Li, Junmei ;

Zhang, Yong ;

Xu, Fan ;

Shen, Qi .

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 [J].

Cardoso, Joao M. S. ;

Royo, Beatriz .

CHEMICAL COMMUNICATIONS, 2012, 48 (41) :4944-4946

[7] Sustainable metal catalysis with iron: From rust to a rising star? [J].

Enthaler, Stephan ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3317-3321

[8]

Guilman A., 1990, PHARMACOL BASIS THER, P899

[9] Guanidines in organic synthesis [J].

Ishikawa, T ;

Kumamoto, T .

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

← 1 2 3 4 →