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

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Abstract

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.

Original languageEnglish
Pages (from-to)1084-1087
Number of pages4
JournalChemistry Letters
Volume49
Issue number9
DOIs
Publication statusPublished - Jun 2020

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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