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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

Authors

Shaoqun Zhu

Atchutarao Pathigoolla

Grace Lowe

DARREN WALSH DARREN.WALSH@NOTTINGHAM.AC.UK
Professor of Chemistry

Mick Cooper

William Lewis

HON LAM Hon.Lam@nottingham.ac.uk
Professor of Sustainable Chemistry



Abstract

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.

Citation

Zhu, S., Pathigoolla, A., Lowe, G., Walsh, D. A., Cooper, M., Lewis, W., & Lam, H. W. (2017). Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF. Chemistry - A European Journal, 23(69), https://doi.org/10.1002/chem.201704380

Journal Article Type Article
Acceptance Date Sep 21, 2017
Online Publication Date Nov 16, 2017
Publication Date Dec 11, 2017
Deposit Date Oct 5, 2017
Publicly Available Date Mar 28, 2024
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 23
Issue 69
DOI https://doi.org/10.1002/chem.201704380
Public URL https://nottingham-repository.worktribe.com/output/899695
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201704380/abstract

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