Literature DB >> 11843596

Copper-catalyzed coupling of alkylamines and aryl iodides: an efficient system even in an air atmosphere.

Fuk Yee Kwong1, Artis Klapars, Stephen L Buchwald.   

Abstract

[reaction: see text] A mild method for the copper-catalyzed amination of aryl iodides is reported. This operationally simple C-N bond-forming protocol uses CuI as the catalyst and ethylene glycol as ligand in 2-propanol. A variety of functionalized aryl iodides as well as several amines were efficiently coupled using this method. This catalytic amination procedure is relatively insensitive to moisture and can be performed under an air atmosphere with comparable yield. Preliminary results on the amination of aryl bromides are also described.

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Year:  2002        PMID: 11843596     DOI: 10.1021/ol0171867

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  25 in total

1.  Cu(I)-amido complexes in the Ullmann reaction: reactions of Cu(I)-amido complexes with iodoarenes with and without autocatalysis by CuI.

Authors:  Ramesh Giri; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-10-26       Impact factor: 15.419

2.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

3.  Dual RXR Agonists and RAR Antagonists Based on the Stilbene Retinoid Scaffold.

Authors:  Claudio Martínez; Michele Lieb; Susana Alvarez; Fátima Rodríguez-Barrios; Rosana Alvarez; Harshal Khanwalkar; Hinrich Gronemeyer; Angel R de Lera
Journal:  ACS Med Chem Lett       Date:  2014-03-19       Impact factor: 4.345

4.  Computational explorations of mechanisms and ligand-directed selectivities of copper-catalyzed Ullmann-type reactions.

Authors:  Gavin O Jones; Peng Liu; K N Houk; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

5.  Mechanism of the Ullmann Biaryl Ether Synthesis Catalyzed by Complexes of Anionic Ligands: Evidence for the Reaction of Iodoarenes with Ligated Anionic CuI Intermediates.

Authors:  Ramesh Giri; Andrew Brusoe; Konstantin Troshin; Justin Y Wang; Marc Font; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-05       Impact factor: 15.419

6.  Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines.

Authors:  Christian Wolf; Shuanglong Liu; Xuefeng Mei; Adam T August; Michael D Casimir
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

7.  Mechanistic studies on the copper-catalyzed N-arylation of amides.

Authors:  Eric R Strieter; Brijesh Bhayana; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

8.  Selective histone deacetylase 6 inhibitors bearing substituted urea linkers inhibit melanoma cell growth.

Authors:  Joel A Bergman; Karrune Woan; Patricio Perez-Villarroel; Alejandro Villagra; Eduardo M Sotomayor; Alan P Kozikowski
Journal:  J Med Chem       Date:  2012-10-23       Impact factor: 7.446

9.  CuCl2-catalyzed one-pot formation of tetrahydroquinolines from N-methyl-N-alkylanilines and vinyl ethers in the presence of t-butylhydroperoxide.

Authors:  Xianghua Yang; Chanjuan Xi; Yanfeng Jiang
Journal:  Molecules       Date:  2006-12-20       Impact factor: 4.411

10.  Regioselective Copper-catalyzed C-N and C-S Bond Formation using Amines, Thiols and Halobenzoic Acids.

Authors:  Shuanglong Liu; John Paul C Pestano; Christian Wolf
Journal:  Synthesis (Stuttg)       Date:  2007-11-16       Impact factor: 3.157

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