Synthesis of Cycloparaphenyleneacetylene via Alkyne Metathesis: C Complexation and Copper-Free Triple Click Reaction.

J Am Chem Soc

Beckman Institute for Advanced Science and Technology, ‡Department of Chemistry, ∥School of Chemical Sciences, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States.

Published: October 2016

AI Article Synopsis

  • Alkyne metathesis was used successfully to create a cycloparaphenyleneacetylene derivative through an effective macrocyclization process, yielding high product amounts.
  • The structure of the derivative allowed for a close fit with carbon (C), indicating a strong interaction that adjusted the arrangement of the component.
  • Strained alkynes facilitated a copper-free reaction, resulting in a 3-fold azide-alkyne cycloaddition at a temperature of 50 °C.

Article Abstract

Alkyne metathesis provided an efficient macrocyclization route to a cycloparaphenyleneacetylene derivative in high yield. The cavity size was suitably matched for C which was tightly bound in an induced-fit fashion. The strained alkynes enabled a copper-free, 3-fold azide-alkyne cycloaddition at 50 °C.

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http://dx.doi.org/10.1021/jacs.6b08752DOI Listing

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