Synthesis of 9-hydroxytriptycenes bearing a functionalized substituent at the c-10 position through a triple cycloaddition reaction of ynolates derived from 2,6-di-tert-butylphenyl esters

Herein, we report the synthesis of various 9-hydroxytriptycenes bearing a functionalized substituent at the C-10 position through a one-pot triple cycloaddition reaction of ynolates with arynes, followed by their functional transformation. Ynolates bearing a functionalized substituent were generated through a double deprotonation method utilizing various readily available sterically hindered esters recently developed by our group. Upon transformation of 1,8,13-trisilyl- or trimethoxy triptycenes, not only the C-1, C-8, C-9, and C-13 (front-side) but also C-10 (back-side) positions of the triptycene products could be functionalized.