A General and Efficient Copper Catalyst for the Amidation of Aryl Halides
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- 25 May 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (25) , 7421-7428
- https://doi.org/10.1021/ja0260465
Abstract
An experimentally simple and inexpensive catalyst system was developed for the amidation of aryl halides by using 0.2−10 mol % of CuI, 5−20 mol % of a 1,2-diamine ligand, and K3PO4, K2CO3, or Cs2CO3 as base. Catalyst systems based on N,N‘-dimethylethylenediamine or trans-N,N‘-dimethyl-1,2-cyclohexanediamine were found to be the most active even though several other 1,2-diamine ligands could be used in the easiest cases. Aryl iodides, bromides, and in some cases even aryl chlorides can be efficiently amidated. A variety of functional groups are tolerated in the reaction, including many that are not compatible with Pd-catalyzed amidation or amination methodology.Keywords
This publication has 39 references indexed in Scilit:
- 3-Aryl-2-oxazolidinones through the Palladium-Catalyzed N-Arylation of 2-OxazolidinonesOrganic Letters, 2001
- Palladium-catalyzed reaction of aryl halides with ureasTetrahedron Letters, 2001
- Palladium catalysed amination of electron deficient halothiophenesTetrahedron Letters, 2000
- Palladium-Catalyzed Intermolecular Coupling of Aryl Halides and AmidesOrganic Letters, 2000
- Synthesis of novel (bis)(diarylamino)thiophenes via palladium-catalysed reaction of (di)bromothiophenes with diarylaminesChemical Communications, 2000
- Palladium-catalyzed coupling of lactams with bromobenzenesTetrahedron Letters, 1999
- Nickel-Catalyzed Amination of Aryl ChloridesJournal of the American Chemical Society, 1997
- Solid phase synthesis of aryl amines via palladium catalyzed amination of resin-bound aromatic bromidesTetrahedron Letters, 1996
- Ueber Phenylirungen bei Gegenwart von Kupfer als KatalysatorEuropean Journal of Inorganic Chemistry, 1906
- Ueber eine neue Bildungsweise von DiphenylaminderivatenEuropean Journal of Inorganic Chemistry, 1903