Regioselective One‐Pot Synthesis of Triptycenes via Triple‐Cycloadditions of Arynes to Ynolates

We developed the novel one‐pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four‐step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucl...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-01, Vol.56 (5), p.1298-1302
Main Authors: Umezu, Satoshi, dos Passos Gomes, Gabriel, Yoshinaga, Tatsuro, Sakae, Mikei, Matsumoto, Kenji, Iwata, Takayuki, Alabugin, Igor, Shindo, Mitsuru
Format: Article
Language:English
Subjects:
Anthracene
aryne
Chelation
directing effect
hyperconjugation
Nucleophiles
Regioselectivity
Ring opening
triptycene
ynolate
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Summary:We developed the novel one‐pot synthetic method of substituted triptycenes by the reaction of ynolates and arynes. This four‐step process involves three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o‐benzyne in the same predictable manner controlled by chelation and negative hyperconjugation. The resulting functionalized C3‐symmetrical triptycenes hold promise in the design of functional materials. Three alkynes and one triple bond: The title reaction constitutes a four‐step process involving three cycloadditions and electrocyclic ring opening of the strained Dewar anthracene. Each of the three related but structurally distinct classes of nucleophiles (ynolate, enolate, and anthracenolate) reacts with o‐benzyne in the same predictable manner controlled by chelation and negative hyperconjugation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201609111