Concise synthesis of phenanthrene derivatives via intermolecular TDDA reaction induced by tetrayne cyclization

Abstract

The facile construction of phenanthrene derivatives through the intermoletetradehydro-Diels-Alder (TDDA) reaction of benzyne in situ generated by the hexadehydro-Diels–Alder (HDDA) reaction with various substituted phenylacetylene was described. The naphthalene derivatives were obtained unexpectedly in another reaction modle when expanding substrate scope. The reaction profiles has good chemoselectivity and provided a new way for the synthesis of highly functionalized phenanthrene and naphthalene derivatives from simple materials under relatively mild conditions.