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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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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cited_by cdi_FETCH-LOGICAL-c5041-9d144bd723a2792bfa2ba95f02148b869032aadf27c1d6b5045056479f16136e3
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container_title Angewandte Chemie International Edition
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creator Umezu, Satoshi
dos Passos Gomes, Gabriel
Yoshinaga, Tatsuro
Sakae, Mikei
Matsumoto, Kenji
Iwata, Takayuki
Alabugin, Igor
Shindo, Mitsuru
description 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.
doi_str_mv 10.1002/anie.201609111
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source Wiley-Blackwell Read & Publish Collection
subjects Anthracene
aryne
Chelation
directing effect
hyperconjugation
Nucleophiles
Regioselectivity
Ring opening
triptycene
ynolate
title Regioselective One‐Pot Synthesis of Triptycenes via Triple‐Cycloadditions of Arynes to Ynolates
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