A highly efficient memantine-modified palladium catalyst for Suzuki-Miyaura cross-coupling reaction

A new simple Pd(memantine)(2)Cl-2 complex was synthesized and characterized by H-1 NMR, C-13 NMR and X-ray single crystal structure determination. The Suzuki-Miyaura reaction of aryl bromides catalyzed by Pd(memantine)(2)Cl-2 complex was investigated in air with different temperature. The high turnover numbers of 650,000 have been obtained in the reaction of 4-bromonitrobenzene with phenylboronic acid at 80 degrees C. At room temperature, the complex also showed high activity for Suzuki-Miyaura cross-coupling reaction of aryl bromides with a wide range of functional groups under air, and the turnover number of up to 99,000 was achieved. The catalytic system also gives good yields toward the reaction of several heteroaryl bromides with thiophenylboronic acid. (C) 2014 Elsevier Ltd. All rights reserved.