Efficient Copper-Catalyzed Direct Amination of Aryl Halides Using Aqueous Ammonia in Water

The N 2 ,N 2 '-diisopropyloxalohydrazide/CuO system efficiently catalyzed the direct amination of aryl bromides and iodides with aqueous ammonia in water at 60 °C in 24 h or at 120 °C in only 20―30 min. Both activated and unactivated aryl and heteroaryl bromides and iodides were readily aminated in good to excellent yields.

[1]  S. Zimmerman,et al.  Room temperature, copper-catalyzed amination of bromonaphthyridines with aqueous ammonia. , 2010, The Journal of organic chemistry.

[2]  Jianwei Xie,et al.  Pyrrole‐2‐carbohydrazides as Ligands for Cu‐Catalyzed Amination of Aryl Halides with Amines in Pure Water , 2010 .

[3]  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.

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

[5]  M. Stradiotto,et al.  A highly versatile catalyst system for the cross-coupling of aryl chlorides and amines. , 2010, Chemistry.

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

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

[8]  Q. Guo,et al.  Room-temperature copper-catalyzed carbon-nitrogen coupling of aryl iodides and bromides promoted by organic ionic bases. , 2009, Angewandte Chemie.

[9]  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.

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

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

[12]  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.

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

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

[15]  M. Taillefer,et al.  A very simple copper-catalyzed synthesis of anilines by employing aqueous ammonia. , 2009, Angewandte Chemie.

[16]  C. L. Macdonald,et al.  Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst. , 2008, Chemical communications.

[17]  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.

[18]  J. Renaud,et al.  Highly efficient and economic synthesis of new substituted amino-bispyridyl derivatives via copper and palladium catalysis , 2008 .

[19]  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.

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

[21]  S. Lawrence Amines: Synthesis, Properties and Applications , 2004 .

[22]  C. J. Knill,et al.  Comprehensive Organic Transformations: A Guide to Functional Group Preparations (2nd ed): R. C. Larock, John Wiley & Sons, Inc., New York, 1999, xliii+2583 pp., £96.99, ISBN 0-471-19031-4 , 2001 .

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