Gieman, Hanaa, Arepally, Sagar and Wirth, Thomas  ORCID: https://orcid.org/0000-0002-8990-0667
2026.
Electrochemical regioselective chalcogenocyclizations of 2‐alkynylbenzamides in flow.
ChemElectroChem
13
(8)
, e202500471.
10.1002/celc.202500471
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License URL: http://creativecommons.org/licenses/by/4.0/
License Start date: 15 April 2026
Official URL: https://doi.org/10.1002/celc.202500471
Abstract
Electrochemical activation plays a key role in boosting substrate reactivity and directing unique cyclization patterns through the nature of intermediates. We report regioselective electrochemical selenocyclizations of ortho‐alkynylbenzamides using diphenyl dichalcogenides in flow. The method enables exclusive 6‐endo‐dig cyclizations under mild and metal‐free conditions. Cyclic voltammetry and control experiments reveal that the oxidation potential of the substrates governs product selectivity. Mechanistic studies suggest that electrophilic selenium species activate alkynes via seleniranium intermediates. This sustainable approach offers a scalable route to selenium‐containing heterocycles with high selectivity and efficiency.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Chemistry |
| Additional Information: | License information from Publisher: LICENSE 1: URL: http://creativecommons.org/licenses/by/4.0/ |
| Publisher: | Wiley |
| ISSN: | 2196-0216 |
| Funders: | EPSRC |
| Projects: | EP/T019719/1 |
| Date of First Compliant Deposit: | 21 April 2026 |
| Date of Acceptance: | 9 March 2026 |
| Last Modified: | 25 Aug 2026 21:57 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/186528 |
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