Radical Dearomatising Spirocyclisation of Benzisoxazole-Tethered Ynones

Nantachai Inprung, Adrian C. Whitwood, Richard J.K. Taylor, Michael J. James*, William P. Unsworth*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The dearomative spirocyclisation of benzisoxazoles through a radical chain mechanism is described. Densely functionalised spirocycles were prepared in high yields by reacting benzisoxazole-tethered ynones with aryl thiols in 1,2-dichloroethane (DCE) at 60 °C. The identification of stabilising three-electron interactions was key to the development of this new radical cascade reaction. The obtained spirocyclic products were converted into other spirocyclic scaffolds through a two-step hydrogenolysis-cyclisation sequence.

Original languageEnglish
Article numbere202300603
JournalEuropean Journal of Organic Chemistry
Early online date27 Sept 2023
Publication statusE-pub ahead of print - 27 Sept 2023

Bibliographical note

Funding Information:
The authors would like to thank the Development and Promotion of Science and Technology Talents Project (DPST), Royal Thai Government. (N.I. EP/N035119/1), the University of York, and the University of Manchester for financial support. We would also like to thank Prof. Victor Chechik for helpful discussions.

Publisher Copyright:
© 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.


  • cascade
  • dearomatisation
  • radical
  • ring expansion
  • spirocyclisation

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