Synthesis of meta-Terphenyl-2,2′′-diols by Anodic C−C Cross-Coupling Reactions

The anodic C−C cross‐coupling reaction is a versatile synthetic approach to symmetric and non‐symmetric biphenols and arylated phenols. We herein present a metal‐free electrosynthetic method that provides access to symmetric and non‐symmetric meta‐terphenyl‐2,2′′‐diols in good yields and high select...

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Veröffentlicht in:Angewandte Chemie International Edition 2016-08, Vol.55 (36), p.10872-10876
Hauptverfasser: Lips, Sebastian, Wiebe, Anton, Elsler, Bernd, Schollmeyer, Dieter, Dyballa, Katrin M., Franke, Robert, Waldvogel, Siegfried R.
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Sprache:eng
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Zusammenfassung:The anodic C−C cross‐coupling reaction is a versatile synthetic approach to symmetric and non‐symmetric biphenols and arylated phenols. We herein present a metal‐free electrosynthetic method that provides access to symmetric and non‐symmetric meta‐terphenyl‐2,2′′‐diols in good yields and high selectivity. Symmetric derivatives can be obtained by direct electrolysis in an undivided cell. The synthesis of non‐symmetric meta‐terphenyl‐2,2′′‐diols required two electrochemical steps. The reactions are easy to conduct and scalable. The method also features a broad substrate scope, and a large variety of functional groups are tolerated. The target molecules may serve as [OCO]3− pincer ligands. Two selective couplings enable the generation of meta‐terphenyl‐2,2′′‐diols in a metal‐ and reagent‐free manner in an electrosynthetic process. The reactions are scalable and very simple to perform and provide access to precursors for pincer ligands.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201605865