Scandium Triflate Catalyzed Cycloadditions of Vinyl Diazo Compounds and In Situ Formed Naphthoquinone Methides

Abstract

Vinyl diazo carbonyl compounds have received great attention and are widely employed in the cycloadditions of in situ formed reactive intermediates. Metal carbenes are predominantly involved in cycloadditions, and transformations of vinyl diazo compounds that do not proceed via the metal carbene pathway have been seldom reported. Herein, scandium-catalyzed cycloadditions of vinyl diazo compounds and in situ formed 2-naphthoquinone-8-methides are achieved, and naphthalene-fused polycyclic products were obtained in up to 88% yield. In the transformation, the nucleophilic conjugate addition of vinyl diazo compounds to in situ formed 2-naphthoquinone-8-methides generates vinyl diazonium intermediates, which undergo an intramolecular Friedel–Crafts reaction and intramolecular transesterification to yield the final product.