Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF
The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of T...
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| Format: | Article |
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Wiley
2017
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| Online Access: | https://eprints.nottingham.ac.uk/46991/ |
| _version_ | 1848797443815112704 |
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| author | Zhu, Shaoqun Pathigoolla, Atchutarao Lowe, Grace Walsh, Darren A. Cooper, Mick Lewis, William Lam, Hon Wai |
| author_facet | Zhu, Shaoqun Pathigoolla, Atchutarao Lowe, Grace Walsh, Darren A. Cooper, Mick Lewis, William Lam, Hon Wai |
| author_sort | Zhu, Shaoqun |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of THF as the solvent is critical for successful reactions. The proposed mechanism of radical initiation involves the photosensitized formation of a triplet sulfonyl nitrene, which abstracts a hydrogen atom from THF to give a tetrahydrofuran-2-yl radical, which then reacts with the sulfonyl azide to generate the sulfonyl radical. |
| first_indexed | 2025-11-14T20:03:58Z |
| format | Article |
| id | nottingham-46991 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:03:58Z |
| publishDate | 2017 |
| publisher | Wiley |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-469912020-05-04T19:22:20Z https://eprints.nottingham.ac.uk/46991/ Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF Zhu, Shaoqun Pathigoolla, Atchutarao Lowe, Grace Walsh, Darren A. Cooper, Mick Lewis, William Lam, Hon Wai The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of THF as the solvent is critical for successful reactions. The proposed mechanism of radical initiation involves the photosensitized formation of a triplet sulfonyl nitrene, which abstracts a hydrogen atom from THF to give a tetrahydrofuran-2-yl radical, which then reacts with the sulfonyl azide to generate the sulfonyl radical. Wiley 2017-12-11 Article PeerReviewed Zhu, Shaoqun, Pathigoolla, Atchutarao, Lowe, Grace, Walsh, Darren A., Cooper, Mick, Lewis, William and Lam, Hon Wai (2017) Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF. Chemistry - A European Journal, 23 (69). pp. 17598-17604. ISSN 1521-3765 http://onlinelibrary.wiley.com/doi/10.1002/chem.201704380/abstract doi:10.1002/chem.201704380 doi:10.1002/chem.201704380 |
| spellingShingle | Zhu, Shaoqun Pathigoolla, Atchutarao Lowe, Grace Walsh, Darren A. Cooper, Mick Lewis, William Lam, Hon Wai Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF |
| title | Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF |
| title_full | Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF |
| title_fullStr | Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF |
| title_full_unstemmed | Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF |
| title_short | Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF |
| title_sort | sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in thf |
| url | https://eprints.nottingham.ac.uk/46991/ https://eprints.nottingham.ac.uk/46991/ https://eprints.nottingham.ac.uk/46991/ |