Accelerated syntheses of amine-bis(phenol) ligands in polyethylene glycol or “on water” under microwave irradiation

Kerton, Francesca M. and Holloway, Stacey and Power, Angela and Soper, R. Graeme and Sheridan, Kristina and Lynam, Jason M. and Whitwood, Adrian C. and Willans, Charlotte E. (2008) Accelerated syntheses of amine-bis(phenol) ligands in polyethylene glycol or “on water” under microwave irradiation. Canadian Journal of Chemistry, 86 (5). pp. 435-443. ISSN 1480-3291

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Abstract

Pure amine-bis(phenol) ligands are readily accessible in high yield, often >90%, when the Mannich condensation reactions are performed “on water” or in poly(ethyleneglycol) (PEG). Microwave-assisted synthesis dramatically reduces the time and energy required to prepare these molecules, typically from 24 h to 5 min. The approach seems to be widely applicable (7 amines and 5 phenols were tested to yield a diverse set of bis(phenol) ligands). Significant improvements in yield were observed for ligands derived from di-tert-amyl and di-tert-butyl phenols, possibly resulting from a hydrophobic effect. Single crystal X-ray diffraction data for the ligand derived from p-cresol and N,N′-dimethylethylenediamine is reported.

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