Abstract
The influence of chelating amine ligands, copper precursors, and solvent composition on copper-catalyzed oxidative coupling of 2,6-dimethylphenol was investigated. The most efficient catalytic reaction was conducted with CuCl2-di-tert-butylethylenediamine (Dt-BEDA) complex in anisole or toluene with alcohol cosolvent. Slight structural changes in the N-substituent, backbone, or coordination atom of the ligand significantly dropped catalytic activities, leading to a low polymer yield. Alcohol cosolvent was necessary to synthesize a polymer of high molecular weight \(\left( {\overline {M_n } > 10,000} \right)\) with the copper(II) catalyst in toluene. With increasing alcohol ratios, the isolated yields and \(\overline {M_n }\) values of the resulting polymers gradually decreased. However, the use of sterically bulky t-butanol produced polymers of the desired molecular weight ranges with low polydispersity indexes (PDI, <2) and without a significant drop in isolated yield. Open image in new window
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