Quell Thomas, Mirion Michael, Schollmeyer Dieter, Dyballa Katrin M, Franke Robert, Waldvogel Siegfried R
Department of Organic Chemistry Johannes Gutenberg University Mainz Duesbergweg 10-14 55128 Mainz Germany.
Evonik Performance Materials GmbH Paul-Baumann-Straße 1 45772 Marl Germany.
ChemistryOpen. 2015 Dec 11;5(2):115-9. doi: 10.1002/open.201500206. eCollection 2016 Apr.
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.
双酚是有机催化中配体体系的重要结构基序，因此属于所谓“优势配体”类别。我们开发了一种新的合成途径，通过使用二氧化硒（一种稳定、强大且可商购的氧化剂）来构建这些结构。我们新的且易于操作的方法根据所使用的溶剂生成双酚和二芳基硒化物。在乙酸中对酚进行氧化处理可得到相应的双酚，而在吡啶中转化则优先形成二芳基硒化物。因此，我们能够分离出多种新型二芳基硒化物，它们可作为钳状配体在有机合成中进一步应用，或作为过渡金属催化中的配体。
