Formation of Arenes via Diallylarenes: Strategic Utilization of Suzuki–Miyaura Cross‐Coupling, Claisen Rearrangement and Ring‐Closing Metathesis

Abstract

AbstractTwo new synthetic strategies for benzoannulation are reported. The first strategy is based on the Suzuki–Miyaura cross‐coupling reaction. To this end, various ortho‐diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring‐closing metathesis (RCM) and one‐pot dichlorodicyanoquinone (DDQ) oxidation sequence to deliver 2‐substituted naphthalenes. In the second strategy, a double Claisen rearrangement and RCM protocol have been used as key steps to give highly functionalized benzoannulated quinone derivatives.