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Updated: Sep 15, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
One-Pot Synthesis of Iptycenes and Dissymmetric Triptycenes Using Ynolate-Benzyne Triple Cycloaddition
Takayuki Iwata1, Shunsuke Furihata2, Takuto Fukami2
1Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugako-en, Kasuga, Fukuoka 816-8580, Japan.
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.
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