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Flow synthesis of triptycene was achieved using triple cycloaddition of ynolate to benzyne. Employing the borate-type benzyne precursor, side reactions triggered by the addition of alkyllithium to benzyne were efficiently suppressed under microflow conditions, thus producing triptycene with a higher yield than that obtained under the corresponding batch conditions. Furthermore, ynolate prepared from α,α-dibromoester under microflow conditions was continuously added to the flow reaction with benzyne, which successfully synthesized triptycene in only one minute.

Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne