One-Pot Synthesis of Iptycenes and Dissymmetric Triptycenes Using Ynolate-Benzyne Triple Cycloaddition

Iptycenes such as noniptycenes, heptiptycenes, pentiptycenes as well as dissymmetric triptycenes having three different aryl groups have been synthesized in a one-pot manner using triple cycloaddition of ynolate with benzynes. The method consists of two-stages involving (1) <i>in situ</i> formation of anthranoxide via double [2 + 2] cycloaddition of ynolate with benzynes and (2) a Diels-Alder reaction of anthranoxide with another benzyne. This method enables rapid access to higher order iptycenes and dissymmetric triptycenes, which have been conventionally synthesized in much longer steps.