Formation of arenes via diallylarenes: strategic utilization of Suzuki-Miyaura cross-coupling, claisen rearrangement and ring-closing metathesis

Abstract

Two 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.