Flow Synthesis of Triptycene via Triple Cycloaddition of Ynolate to Benzyne

Takayuki Iwata, Tatsuro Yoshinaga, Mitsuru Shindo

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1903-1906
Number of pages4
JournalSynlett
Volume31
Issue number19
DOIs
Publication statusPublished - Dec 1 2020

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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