Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF

Zhu, Shaoqun and Pathigoolla, Atchutarao and Lowe, Grace and Walsh, Darren A. and Cooper, Mick and Lewis, William and Lam, Hon Wai (2017) Sulfonylative and azidosulfonylative cyclizations by visible-light-photosensitization of sulfonyl azides in THF. Chemistry - A European Journal . ISSN 1521-3765 (In Press)

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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.

Item Type: Article
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/chem.201704380
Depositing User: Eprints, Support
Date Deposited: 05 Oct 2017 10:43
Last Modified: 18 Oct 2017 18:57
URI: http://eprints.nottingham.ac.uk/id/eprint/46991

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