Amination of Aryl Halides by Using an Environmentally Benign, Recyclable Copper Catalyst

The combination of CuSO4 with naturally occurring sucrose in a biodegradable aqueous solution of PEG-200 has been confirmed as a novel, recyclable, and environmentally benign homogeneous catalyst system for the direct amination of aryl halides with NH3·H2O. Electron-rich, electron-poor, and even ortho-substituted aryl bromides and iodides could be aminated to provide the desired primary arylamines in high yields at 90 °C without the need of an inert atmosphere.

[1]  H. Neumann,et al.  Recyclable catalysts for palladium-catalyzed aminations of aryl halides. , 2011, Chemistry.

[2]  Jianwei Xie,et al.  A Highly Versatile Catalytic System for N-Arylation of Amines with Aryl Chlorides in Water , 2011 .

[3]  T. Yuan,et al.  Simple and efficient CuI/PEG-400 system for amination of aryl halides with aqueous ammonia , 2011 .

[4]  D. Ganapathy,et al.  D-Glucosamine as a green ligand for copper catalyzed synthesis of primary aryl amines from aryl halides and ammonia. , 2011, Chemical communications.

[5]  Huajian Xu,et al.  CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution. , 2011, The Journal of organic chemistry.

[6]  J. Hartwig,et al.  Catalytic organometallic reactions of ammonia. , 2011, Angewandte Chemie.

[7]  Andrea R. Gerson,et al.  Resolving surface chemical states in XPS analysis of first row transition metals, oxides and hydroxides: Sc, Ti, V, Cu and Zn , 2010 .

[8]  Jianwei Xie,et al.  Efficient Copper-Catalyzed Direct Amination of Aryl Halides Using Aqueous Ammonia in Water , 2010 .

[9]  J. Renaud,et al.  Direct amination of aryl halides with ammonia. , 2010, Chemical Society reviews.

[10]  M. Stradiotto,et al.  A P,N-ligand for palladium-catalyzed ammonia arylation: coupling of deactivated aryl chlorides, chemoselective arylations, and room temperature reactions. , 2010, Angewandte Chemie.

[11]  Di Wu,et al.  A Simple and Efficient Catalytic System for Coupling Aryl Halides with Aqueous Ammonia in Water , 2010 .

[12]  J. Renaud,et al.  Efficient synthesis of aminopyridine derivatives by copper catalyzed amination reactions. , 2010, Chemical communications.

[13]  Xiao‐Feng Wu,et al.  Ligand-Free Iron/Copper-Cocatalyzed Amination of Aryl Iodides , 2009 .

[14]  J. Hartwig,et al.  Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: a general method for the preparation of primary arylamines. , 2009, Journal of the American Chemical Society.

[15]  Deping Wang,et al.  An Efficient Copper-Catalyzed Amination of Aryl Halides by Aqueous Ammonia , 2009 .

[16]  C. Wolf,et al.  Efficient copper-catalyzed coupling of aryl chlorides, bromides and iodides with aqueous ammonia. , 2009, Chemical communications.

[17]  Yongwen Jiang,et al.  CuI/4-hydro-L-proline as a more effective catalytic system for coupling of aryl bromides with N-boc hydrazine and aqueous ammonia. , 2009, The Journal of organic chemistry.

[18]  A. Börner,et al.  A general palladium-catalyzed amination of aryl halides with ammonia. , 2009, Chemistry.

[19]  Limin Wang,et al.  Hemilabile-coordinated copper promoted amination of aryl halides with ammonia in aqueous ethylene glycol under atmosphere pressure , 2009 .

[20]  G. Evano,et al.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis. , 2008, Chemical reviews.

[21]  Sukbok Chang,et al.  Ammonium salts as an inexpensive and convenient nitrogen source in the Cu-catalyzed amination of aryl halides at room temperature. , 2008, Chemical communications.

[22]  S. Buchwald,et al.  Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines. , 2007, Journal of the American Chemical Society.

[23]  A. J. Sobral,et al.  Interactions of copper (II) chloride with sucrose, glucose, and fructose in aqueous solutions , 2007 .

[24]  J. Hartwig,et al.  Palladium-catalyzed coupling of ammonia and lithium amide with aryl halides. , 2006, Journal of the American Chemical Society.

[25]  D. Zewge,et al.  Amination of aryl halides using copper catalysis , 2001 .