Abstract
Herein we report an electrochemical deconstructive functionalization approach for the synthesis of C(sp3)-rich heterocycles. The reaction proceeds via the mesolytic cleavage of anodically generated aromatic radical cations and the trapping of formed carbocation intermediates with internal nucleophiles. The method has been demonstrated across various arylalcohol substrates to access a diverse range of C(sp3)-rich heterocycles including tetrahydrofuran, tetrahydropyran, and pyrrolidine scaffolds (26 examples). The electrochemical method was demonstrated on a 5 mmol scale via single pass continuous flow, which utilized lower supporting electrolyte concentration and exhibited increased productivity in relation to the batch process.
| Original language | English |
|---|---|
| Pages (from-to) | 9051-9055 |
| Number of pages | 5 |
| Journal | Organic Letters |
| Volume | 26 |
| Issue number | 42 |
| Early online date | 21 Oct 2024 |
| DOIs | |
| Publication status | Published - 25 Oct 2024 |
Bibliographical note
Publisher Copyright:© 2024 The Authors. Published by American Chemical Society.
Data Availability Statement
The data underlying this study are available in the published letter, in its Supporting Information, and openly available in the Cardiff University data catalogue at: 10.17035/cardiff.26362525Funding
We gratefully acknowledge the School of Chemistry at CardiffUniversity and the Department of Chemistry at the Universityof Bath for generous support. We thank the Saudi Arabiacultural mission in the UK and the Department of Chemistryat the University of Bisha (H.A.M.) and the Department ofChemistry at Jazan University (A.H.H.) for PhD studentships.We also thank the Government of India, Ministry of TribalAffairs, for a National Overseas Scholarship (NOS) (K.M.)
| Funders | Funder number |
|---|---|
| Ministry of Tribal Affairs |