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Spontaneous trisulfide metathesis in polar aprotic solvents

Date

2026

Authors

Patel, H.D.
Tikoalu, A.D.
Smith, J.N.
Pei, Z.
Tonkin, S.J.
Shapter, R.
Yan, P.
Tsoukatos, S.
Bloch, W.M.
Johnston, M.R.

Editors

Advisors

Journal Title

Journal ISSN

Volume Title

Type:

Journal article

Citation

Nature Chemistry, 2026; 1-11

Statement of Responsibility

Harshal D. Patel, Alfrets D. Tikoalu, James N. Smith, Zhipeng Pei, Samuel J. Tonkin, Ryan Shapter, Peiyao Yan, Steven Tsoukatos, Witold M. Bloch, Martin R. Johnston, Jeffrey R. Harmer, Christopher T. Gibson, Michael V. Perkins, Tom Hasell, Michelle L. Coote, Zhongfan Jia and Justin M. Chalker

Conference Name

DOI

10.1038/s41557-026-02091-z

Abstract

Sulfur–sulfur bonds are ubiquitous across broad classes of natural products, peptides and proteins, drug molecules, and synthetic polymers and materials. The ability to make and break these bonds in a controlled manner is critical for their many scientific and technological applications. Here we report the discovery of an unusual S–S metathesis reaction of organic trisulfides. When exposed to certain polar aprotic solvents, trisulfides were found to undergo spontaneous metathesis, with the reaction equilibrium established in seconds in some cases. No exogenous reagents, heat, light or other stimuli were required to provoke this reaction. Furthermore, the trisulfide metathesis process can occur both inter- and intramolecularly. Understanding the scope and mechanism of this reaction enabled diverse applications of this chemistry in dynamic combinatorial library synthesis, the covalent modification of complex natural products, and S–S metathesis polymerization and depolymerization as a platform for chemically recyclable plastics.

School/Discipline

Dissertation Note

Provenance

Description

OnlinePubl

Access Status

Rights

© The Author(s), under exclusive licence to Springer Nature Limited 2026.

License

Grant ID

http://purl.org/au-research/grants/arc/DP200100090
 http://purl.org/au-research/grants/arc/DP230100587
 http://purl.org/au-research/grants/arc/DP240100555
 http://purl.org/au-research/grants/arc/FT220100054
 http://purl.org/au-research/grants/arc/FT240100330
 http://purl.org/au-research/grants/arc/CE230100021

Published Version

https://doi.org/10.1038/s41557-026-02091-z

Call number

Persistent link to this record

https://hdl.handle.net/2440/150163