Skip to main content

Research Repository

See what's under the surface

Advanced Search

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 A. Walsh darren.walsh@nottingham.ac.uk

Mick Cooper

William Lewis

Hon Wai Lam



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.

Journal Article Type Article
Publication Date Dec 11, 2017
Journal Chemistry - A European Journal
Print ISSN 0947-6539
Electronic ISSN 1521-3765
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 23
Issue 69
APA6 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
DOI https://doi.org/10.1002/chem.201704380
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/chem.201704380/abstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

Files

Zhu_et_al-2017-Chemistry_-_A_European_Journal.pdf (1.1 Mb)
PDF

Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





You might also like



Downloadable Citations

;