Unexpected copper mediated benzyl O→O migration during an Ullmann ether coupling |
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Authors: | Corinne Vanucci-Bacqué Slim ChaabouniIsabelle Fabing Florence Bedos-Belval Michel Baltas |
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Institution: | Université Paul Sabatier, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, UMR-CNRS 5068, 118 route de Narbonne, 31062 Toulouse cedex 9, France |
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Abstract: | The synthesis of a highly functionalized phenolic diaryl ether 5,5′-oxybis(4-hydroxy-3-methoxybenzaldehyde) (1) potentially interesting as a new scaffold for drug design, has been carried out using Ullmann coupling conditions. An unusual benzyl migration in o-benzyloxyphenol moiety occurred during this reaction leading to an unexpected compound identified as 4-(benzyloxy)-3-(2-(benzyloxy)-4-formyl-6-methoxyphenoxy)-5-methoxy benzaldehyde (7). A rationale for this migration process is proposed. |
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Keywords: | Diaryl ether Ullmann condensation Benzyl migration Phenol dimers |
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