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 materials make this method to an attractive approach.