Synthesis of Optically Pure Arylamine Derivatives by Using the Bucherer Reaction

The Bucherer reaction is a common pathway for the conversion of 1- and 2-naphthols into the corresponding 1- or 2-naphthylamines, respectively. Mostly, only singular examples for its preparative use are reported since this particular transformation seems to be very sensitive to the reaction conditions. By choosing different phenolic substrates and chiral amines, we were able to prepare a broad scope of optically pure arylamines using this type of reaction. In contrast to alternative methods forming C−N aryl bonds such as Buchwald-Hartwig or Chan-Lam cross-coupling reactions, no palladium or copper catalysts are required. The use of water as solvent and the easily available starting material…

Selective Formation of 4,4'-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction.

A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4'-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4'-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.

Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols

Front Cover: Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols (ChemElectroChem 9/2018)

CCDC 1858697: Experimental Crystal Structure Determination

Related Article: Benedikt Dahms, Philipp J. Kohlpaintner, Anton Wiebe, Rolf Breinbauer, Dieter Schollmeyer, Siegfried R. Waldvogel|2019|Chem.-Eur.J.|25|2713|doi:10.1002/chem.201805737

CCDC 1858698: Experimental Crystal Structure Determination

Related Article: Benedikt Dahms, Philipp J. Kohlpaintner, Anton Wiebe, Rolf Breinbauer, Dieter Schollmeyer, Siegfried R. Waldvogel|2019|Chem.-Eur.J.|25|2713|doi:10.1002/chem.201805737