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

Research output: Contribution to journalArticle

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

Fingerprint

Rhodium
Alkynes
Chirality
Gibbs free energy
8-cycloparaphenylene

ASJC Scopus subject areas

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

Cite this

Synthesis of Belt- A nd Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization. / Nishigaki, Shuhei; Shibata, Yu; Nakajima, Atsuya; Okajima, Hajime; Masumoto, Yui; Osawa, Taisei; Muranaka, Atsuya; Sugiyama, Haruki; Horikawa, Ayano; Uekusa, Hidehiro; Koshino, Hiroyuki; Uchiyama, Masanobu; Sakamoto, Akira; Tanaka, Ken.

In: Journal of the American Chemical Society, 01.01.2019.

Research output: Contribution to journalArticle

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 2019, '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
Nishigaki, Shuhei ; Shibata, Yu ; Nakajima, Atsuya ; Okajima, Hajime ; Masumoto, Yui ; Osawa, Taisei ; Muranaka, Atsuya ; Sugiyama, Haruki ; Horikawa, Ayano ; Uekusa, Hidehiro ; Koshino, Hiroyuki ; Uchiyama, Masanobu ; Sakamoto, Akira ; Tanaka, Ken. / Synthesis of Belt- A nd Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization. In: Journal of the American Chemical Society. 2019.
@article{225d2753b01a4ec8a345b24e08705a2b,
title = "Synthesis of Belt- A nd M{\"o}bius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization",
abstract = "A belt-shaped [8]cycloparaphenylene (CPP) and an enantioenriched M{\"o}bius-shaped [10]CPP have been synthesized by high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This M{\"o}bius-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. {\circledC}",
author = "Shuhei Nishigaki and Yu Shibata and Atsuya Nakajima and Hajime Okajima and Yui Masumoto and Taisei Osawa and Atsuya Muranaka and Haruki Sugiyama and Ayano Horikawa and Hidehiro Uekusa and Hiroyuki Koshino and Masanobu Uchiyama and Akira Sakamoto and Ken Tanaka",
year = "2019",
month = "1",
day = "1",
doi = "10.1021/jacs.9b06197",
language = "English",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",

}

TY - JOUR

T1 - Synthesis of Belt- A nd Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization

AU - Nishigaki, Shuhei

AU - Shibata, Yu

AU - Nakajima, Atsuya

AU - Okajima, Hajime

AU - Masumoto, Yui

AU - Osawa, Taisei

AU - Muranaka, Atsuya

AU - Sugiyama, Haruki

AU - Horikawa, Ayano

AU - Uekusa, Hidehiro

AU - Koshino, Hiroyuki

AU - Uchiyama, Masanobu

AU - Sakamoto, Akira

AU - Tanaka, Ken

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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. ©

AB - 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. ©

UR - http://www.scopus.com/inward/record.url?scp=85072337812&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85072337812&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b06197

DO - 10.1021/jacs.9b06197

M3 - Article

C2 - 31418559

AN - SCOPUS:85072337812

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

ER -