Covalent-Bond-Directed Synthesis of Rotaxanes from Macrocyclic Diaryliodonium Salts

We achieved the synthesis of [2]rotaxane by the reaction of a bulky phenoxide with a macrocyclic iodonium salt, which served as a covalent-bond-tethered precursor. The cleavage of the tether and the formation of the axle component proceeded simultaneously, providing rotaxane in a good yield. The versatility of this approach was demonstrated by the synthesis of [3]rotaxane as well as the synthesis of [2]rotaxane from a medicine.

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Publication Details

Journal
Organic Letters
Published
2026-05-09
DOI
https://doi.org/10.1021/acs.orglett.6c01609
Primary Topic
Supramolecular Chemistry and Complexes
Type
article
Field-Weighted Citation Impact
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article

Covalent-Bond-Directed Synthesis of Rotaxanes from Macrocyclic Diaryliodonium Salts

Shoichi Hosoya, Yusuke Yoshigoe, Tairin Kawasaki, Yuichiro Mutoh et al.
Organic Letters
Supramolecular Chemistry and Complexes
article

Covalent-Bond-Directed Synthesis of Rotaxanes from Macrocyclic Diaryliodonium Salts

Shoichi Hosoya, Yusuke Yoshigoe, Tairin Kawasaki, Yuichiro Mutoh, Shinichi Saito, Kazushi Hamamura, Akari Nakamura
article en

Abstract

We achieved the synthesis of [2]rotaxane by the reaction of a bulky phenoxide with a macrocyclic iodonium salt, which served as a covalent-bond-tethered precursor. The cleavage of the tether and the formation of the axle component proceeded simultaneously, providing rotaxane in a good yield. The versatility of this approach was demonstrated by the synthesis of [3]rotaxane as well as the synthesis of [2]rotaxane from a medicine.

Organic Letters
Tokyo University of Science (JP), Ochanomizu University (JP)
Openalex Percentile: Top 9%
Supramolecular Chemistry and Complexes
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