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Solvent‐Dependent Facile Synthesis of Diaryl Selenides and Biphenols Employing Selenium Dioxide

Biphenols are important structure motifs for ligand systems in organic catalysis and are therefore included in the category of so‐called “privileged ligands”. We have developed a new synthetic pathway to construct these structures by the use of selenium dioxide, a stable, powerful, and commercially...

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Detalles Bibliográficos
Autores principales: Quell, Thomas, Mirion, Michael, Schollmeyer, Dieter, Dyballa, Katrin M., Franke, Robert, Waldvogel, Siegfried R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4906476/
https://www.ncbi.nlm.nih.gov/pubmed/27308222
http://dx.doi.org/10.1002/open.201500206
Descripción
Sumario:Biphenols are important structure motifs for ligand systems in organic catalysis and are therefore included in the category of so‐called “privileged ligands”. We have developed a new synthetic pathway to construct these structures by the use of selenium dioxide, a stable, powerful, and commercially available oxidizer. Our new, and easy to perform protocol gives rise to biphenols and diaryl selenides depending on the solvent employed. Oxidative treatment of phenols in acetic acid yields the corresponding biphenols, whereas conversion in pyridine results in the preferred formation of diaryl selenides. As a consequence, we were able to isolate a broad scope of novel diaryl selenides, which could act as pincer‐like ligands with further applications in organic synthesis or as ligands in transition metal catalysis.