Unexpected copper mediated benzyl OaO migration during an Ullmann ether coupling

The synthesis of a highly functionalized phenolic diaryl ether 5,5a2-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...

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Bibliographic Details
Published in:Tetrahedron letters 2014-01, Vol.55 (2), p.528-530
Main Authors: Vanucci-Bacque, Corinne, Chaabouni, Slim, Fabing, Isabelle, Bedos-Belval, Florence, Baltas, Michel
Format: Article
Language:English
Subjects:
Benzaldehyde
Ethers
Joining
Migration
OAO
Scaffolds
Synthesis
Tetrahedrons
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Summary:The synthesis of a highly functionalized phenolic diaryl ether 5,5a2-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-methox y benzaldehyde (7). A rationale for this migration process is proposed.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2013.11.089