AgOTf-catalyzed electrophilic cyclization of triynols with NXS: rapid synthesis of densely trisubstituted naphthalenes and quinolines.

A silver triflate-catalyzed electrophilic cyclization reaction of acyclic triynols with NXS (X=I, Br) under mild conditions is reported. Three reactive functional groups, such as a carbonyl group, an alkyne group, and a halogen, could be selectively installed at the C1, C2, and C3 positions to obtain the naphthalene and quinoline products, respectively. The obtained densely trisubstituted products could be further transformed into more complex aromatic products by manipulating the alkynyl moiety and the other two functional groups as synthons.