Research Progress on Organic Cation Receptors Based on Molecular Containers

doi:10.6023/cjoc202303028

Abstract

Molecular containers are supramolecular structures that mimic the confined space and active sites of enzymes, attracting broad interest of supramolecular scientists since their emergence. Scientists have developed molecular containers with different sizes and electronic properties, hoping that they can be applied in stabilizing reaction intermediates, capturing active species and catalyzing reactions. A number of representative molecular containers that are widely studied as cation receptors in the supramolecular field are reviewed. They possess the properties of stabilizing active species, regulating reaction activity and enhancing substrate/reaction selectivity by encapsulating cationic species. The recognition behavior of molecular containers and their function of regulating the properties of cationic species are summarized. The principles and rules involved are explained and an outlook on the future development of this field is provided.

Key words: confined space, molecular container, self-assembly, organic cation, catalysis

Cite this article

Wenjie Zhu, Zhenchuang Xu, Yu-Cheng Gu, Yanchuan Zhao. Research Progress on Organic Cation Receptors Based on Molecular Containers[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 2991-3005.

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Fig. & Tab. 23

Scheme 1. Stabilization of tropylium via encapsulation with molecular container

Scheme 2. Stabilization of iminium and phosphonium/ketone adduct using molecular containers

Scheme 3. Stabilization of proton-pump inhibitor with CB[7]

Scheme 4. Stabilization of radical cations with CB[7]

Scheme 5. Cyclization reaction catalyzed by a tetrahedral molecular container

Scheme 6. Azo-Prins cyclization catalyzed by a tetrahedral molecular container

Scheme 7. Nazarov cyclization promoted by a tetrahedral molecular container

Scheme 8. Orthoformate hydrolysis promoted by a tetrahedral molecular container

Scheme 9. Azo-darzens cyclization catalyzed by a tetrahedral molecular container

Scheme 10. Terpene cyclization catalyzed by a hydrogen bonded molecular container

Scheme 11. Acetal hydrolysis promoted by a hydrogen bonded molecular container

Scheme 12. Asymmetric hydrogenation promoted by a hydrogen bonded molecular container

Scheme 13. C—H bonds of aldehydes and ethers promoted by a tetrahedral molecular container

Scheme 14. Olefin isomerization promoted by a tetrahedral molecular container

Scheme 15. Selective olefin hydrogenation mediated by a tetrahedral molecular container

Scheme 16. Hydroalkoxylation catalyzed by a tetrahedral molecular container

Scheme 17. Tandem esterase-catalyzed ester hydrolysis and metal-catalyzed hydroalkoxylation

Scheme 18. Reductive elimination mediated by a tetrahedral molecular container

Scheme 19. Regulation of the catalytic activity of a photoreaction based on a hydrogen-bonded molecular container

Scheme 20. Hydration of terminal alkynes mediated by a hydrogen bonded molecular container

Scheme 21. Regulation of the activity of binuclear gold complexes with a hydrogen-bonded molecular container

Scheme 22. Copper-catalyzed asymmetric Diels-Alder reaction mediated by CB[8]

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