Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes

We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise.