American Chemical Society
jo800818e_si_001.pdf (497.63 kB)

Copper-Catalyzed Synthesis of Primary Arylamines via Cascade Reactions of Aryl Halides with Amidine Hydrochlorides

Download (497.63 kB)
journal contribution
posted on 2008-09-05, 00:00 authored by Xiaoting Gao, Hua Fu, Renzhong Qiao, Yuyang Jiang, Yufen Zhao
We have developed an efficient method for the synthesis of primary arylamines from aryl halides using amidine hydrochlorides as the ammonia surrogates. The protocol uses 10 mol % CuI as the catalyst, 20 mol % l-proline as the ligand, Cs2CO3 as the base, and DMF as the solvent and proceeds the sequential coupling of aryl halides with amidine hydrochlorides and hydrolysis of intermediates to give the target products. This is a convenient, inexpensive, and practical approach to primary arylamines.