Straightforward Synthesis of Novel Acene-Based Aryne Precursors

Large polycyclic o-(trimethylsilyl)aryl triflates are easily obtained by reaction of commercially available bisaryne precursors with cyclopentadienones. The transformation involves controlled generation of one of the aryne functionalities, trapping by Diels-Alder reaction with a dienone, and chelotropic extrusion of CO. The newly synthesized triflates are precursors of acene-based arynes, including a didehydropentacene.