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 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.
Department of Organic Chemistry Johannes Gutenberg University Mainz Duesbergweg 10-14 55128 Mainz Germany.
Thomas
T
Quell
Department of Organic Chemistry Johannes Gutenberg University Mainz Duesbergweg 10-14 55128 Mainz Germany.
Michael
M
Mirion
Department of Organic Chemistry Johannes Gutenberg University Mainz Duesbergweg 10-14 55128 Mainz Germany.
Dieter
D
Schollmeyer
Evonik Performance Materials GmbH Paul-Baumann-Straße 1 45772 Marl Germany.
Katrin M
KM
Dyballa
Evonik Performance Materials GmbH Paul-Baumann-Straße 145772 Marl Germany; Department of Theoretical Chemistry Ruhr-Universität Bochum 44780 Bochum Germany.
Robert
R
Franke
Department of Organic Chemistry Johannes Gutenberg University Mainz Duesbergweg 10-14 55128 Mainz Germany.
Siegfried R
SR
Waldvogel
C−C coupling; arenes; biaryls; catalysis; oxidation; selenium dioxide