High Yielding Synthesis of 2,2'-bipyridine Macrocycles, Versatile Intermediates in the Synthesis of Rotaxanes

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Jul 13

PMID 29997807

Citations 30

Authors

J E M Lewis

R J Bordoli

M Denis

C J Fletcher

M Galli

E A Neal

E M Rochette

S M Goldup

Affiliations

Soon will be listed here.

Abstract

We present an operationally simple approach to 2,2'-bipyridine macrocycles. Our method uses simple starting materials to produce these previously hard to access rotaxane precursors in remarkable yields (typically >65%) across a range of scales (0.1-5 mmol). All of the macrocycles reported are efficiently converted (>90%) to rotaxanes under AT-CuAAC conditions. With the requisite macrocycles finally available in sufficient quantities, we further demonstrate their long term utility through the first gram-scale synthesis of an AT-CuAAC [2]rotaxane and extend this powerful methodology to produce novel Sauvage-type molecular shuttles.

Citing Articles

Multimodal Molecular Motion in the Rotaxanes and Catenanes Incorporating Flexible Calix[n]phyrin Stations.

Grzelczak R, Basak T, Trzaskowski B, Kinzhybalo V, Szyszko B Angew Chem Int Ed Engl. 2024; 64(1):e202413579.

PMID: 39190832 PMC: 11701352. DOI: 10.1002/anie.202413579.

The End of the Beginning of Mechanical Stereochemistry.

Goldup S Acc Chem Res. 2024; 57(12):1696-1708.

PMID: 38830116 PMC: 11191403. DOI: 10.1021/acs.accounts.4c00195.

The Final Stereogenic Unit of [2]Rotaxanes: Type 2 Geometric Isomers.

Savoini A, Gallagher P, Saady A, Goldup S J Am Chem Soc. 2024; 146(12):8472-8479.

PMID: 38499387 PMC: 10979452. DOI: 10.1021/jacs.3c14594.

Dynamic mechanostereochemical switching of a co-conformationally flexible [2]catenane controlled by specific ionic guests.

Yao Y, Tse Y, Kin-Man Lai S, Shi Y, Low K, Au-Yeung H Nat Commun. 2024; 15(1):1952.

PMID: 38433258 PMC: 10909852. DOI: 10.1038/s41467-024-46099-w.

Direct Detection of Hydrogen Bonds in Supramolecular Systems Using H-N Heteronuclear Multiple Quantum Coherence Spectroscopy.

Jinks M, Howard M, Rizzi F, Goldup S, Burnett A, Wilson A J Am Chem Soc. 2022; 144(50):23127-23133.

PMID: 36508201 PMC: 9782782. DOI: 10.1021/jacs.2c10742.

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