N-Heterocyclic carbene as a Brønsted base catalyst for the amination of naphthol derivatives and alcoholysis of glutaric anhydrides

Abstract

A non-covalent Brønsted-basic N-heterocyclic carbene catalyzed (NHC) Friedel-Crafts type amination of naphthol derivatives using dialkyl azodicarboxylates as the aminating source and alcoholysis of various glutaric anhydrides using alcohol as pronucleophile is presented. Both of these reactions are performed in the presence of either commercially available free-carbene catalyst or in situ-generated carbene catalyst. Friedel-Crafts type amination reaction is an example of a hydroxy group facilitated amination reaction. Both reactions proceed via in situ activations of –OH group by the carbene catalyst through hydrogen bonding interaction and furnish the relevant products in moderate to excellent yields.