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

Created on 14 Jul 2025

Authors

Takayuki Iwata, Shunsuke Furihata, Takuto Fukami, Mitsuru Shindo

Published in

Organic letters. Jul 14, 2025. Epub Jul 14, 2025.

Abstract

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) in situ 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.

PMID:
40654010
Bibliographic data and abstract were imported from PubMed on 14 Jul 2025.

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