A general and efficient copper catalyst for the amidation of aryl halides.
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 K(3)PO(4), K(2)CO(3), or Cs(2)CO(3) 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.
Klapars
Artis
A
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Huang
Xiaohua
X
Buchwald
Stephen L
SL
D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003959:Diamines / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry
D000577:Amides; D003959:Diamines; D006841:Hydrocarbons, Aromatic; D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D003300:Copper