Synthesis of Belt- A nd Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization

Shuhei Nishigaki, Yu Shibata, Atsuya Nakajima, Hajime Okajima, Yui Masumoto, Taisei Osawa, Atsuya Muranaka, Haruki Sugiyama, Ayano Horikawa, Hidehiro Uekusa, Hiroyuki Koshino, Masanobu Uchiyama, Akira Sakamoto, Ken Tanaka

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Abstract

A belt-shaped [8]cycloparaphenylene (CPP) and an enantioenriched Möbius-shaped [10]CPP have been synthesized by high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This Möbius-shaped [10]CPP possesses stable chirality and isolated with high enantiomeric purity. It is evident from the reaction Gibbs energy calculation that the above irreversible cyclotrimerizations are highly exothermic; therefore establishing that the intramolecular alkyne cyclotrimerization is a powerful route to strained cyclic molecular strips. ©

Original languageEnglish
JournalJournal of the American Chemical Society
DOIs
Publication statusAccepted/In press - 2019 Jan 1
Externally publishedYes

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Nishigaki, S., Shibata, Y., Nakajima, A., Okajima, H., Masumoto, Y., Osawa, T., Muranaka, A., Sugiyama, H., Horikawa, A., Uekusa, H., Koshino, H., Uchiyama, M., Sakamoto, A., & Tanaka, K. (Accepted/In press). Synthesis of Belt- A nd Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.9b06197