Ho, Hon Eong orcid.org/0000-0003-1037-2505, Pagano, Angela, Rossi-Ashton, James A. et al. (7 more authors) (2020) Visible-light-induced intramolecular charge transfer in the radical spirocyclisation of indole-tethered ynones. Chemical Science. pp. 1353-1360. ISSN 2041-6539
Abstract
Indole-tethered ynones form an intramolecular electron donor-acceptor complex that can undergo visible-light-induced charge transfer to promote thiyl radical generation from thiols. This initiates a novel radical chain sequence, based on dearomatising spirocyclisation with concomitant C-S bond formation. Sulfur-containing spirocycles are formed in high yields using this simple and mild synthetic protocol, in which neither transition metal catalysts nor photocatalysts are required. The proposed mechanism is supported by various mechanistic studies, and the unusual radical initiation mode represents only the second report of the use of an intramolecular electron donor-acceptor complex in synthesis.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Royal Society of Chemistry 2020 |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 21 Feb 2020 09:20 |
Last Modified: | 03 Nov 2024 01:24 |
Published Version: | https://doi.org/10.1039/c9sc05311e |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1039/c9sc05311e |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:157506 |