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Catalysis enabled synthesis, structures, and reactivities of fluorinated S8-corona[n]arenes (n = 8–12)

Turley, Andrew T.; Hanson-Heine, Magnus W. D.; Argent, Stephen P.; Hu, Yaoyang; Jones, Thomas A.; Fay, Michael; Woodward, Simon


Andrew T. Turley

Magnus W. D. Hanson-Heine

Yaoyang Hu

Thomas A. Jones

Professor of Synthetic Organic Chemistry


Previously inaccessible large S8-corona[n]arene macrocycles (n = 8-12) with alternating aryl and 1,4-C6F4 subunits are easily prepared on up to gram scales, without the need for chromatography (up to 45% yield, 10 different examples) through new high acceleration SNAr substitution protocols (catalytic NR4F in pyridine, R = H, Me, Bu). Macrocycle size and functionality are tunable by precursor and catalyst selection. Equivalent simple NR4F catalysis allows facile late-stage SNAr difunctionalisation of the ring C6F4 units with thiols (8 derivatives, typically 95+% yields) providing two-step access to highly functionalised fluoromacrocycle libraries. Macrocycle host binding supports fluoroaryl catalytic activation through contact ion pair binding of NR4F and solvent inclusion. In the solid-state, solvent inclusion also intimately controls macrocycle conformation and fluorine-fluorine interactions leading to spontaneous self-assembly into infinite columns with honeycomb-like lattices.


Turley, A. T., Hanson-Heine, M. W. D., Argent, S. P., Hu, Y., Jones, T. A., Fay, M., & Woodward, S. (2023). Catalysis enabled synthesis, structures, and reactivities of fluorinated S8-corona[n]arenes (n = 8–12). Chemical Science, 14(1), 70-77.

Journal Article Type Article
Acceptance Date Nov 13, 2022
Online Publication Date Nov 16, 2022
Publication Date Jan 7, 2023
Deposit Date Dec 20, 2022
Publicly Available Date Dec 20, 2022
Journal Chemical Science
Print ISSN 2041-6520
Electronic ISSN 2041-6539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 14
Issue 1
Pages 70-77
Public URL
Publisher URL


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