A General and Efficient Copper Catalyst for the Amidation of Aryl Halides
“A General and Efficient Copper Catalyst for the Amidation of Aryl Halides”, J. Am. Chem. Soc., 2002, 124(25), 7421-7428.
An experimentally simple and inexpensive catalyst system was developed for the amidation of aryl halides by using 0.2-10 mol % of Cul, 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.