Issue 1, 2020

Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

Abstract

Metal-free insertion of sulfur dioxide with aryl iodides and silyl enolates or allylic bromide under ultraviolet irradiation at room temperature is accomplished. This protocol provides a convenient route to sulfonated cyclic compounds under mild conditions. Not only N-(2-iodophenyl)-N-methylmethacrylamides but also 1-iodo-2-allenoxybenzene is workable. A plausible mechanism is proposed, which shows that during the reaction process, aryl radicals formed in situ from aryl iodides under ultraviolet irradiation undergo intramolecular 5-exo-cyclization, with subsequent sulfonylation via insertion of sulfur dioxide. The resulting sulfonyl radicals are further trapped by silyl enolates or allylic bromide giving rise to sulfonated cyclic compounds.

Graphical abstract: Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

Supplementary files

Article information

Article type
Research Article
Submitted
22 Oct 2019
Accepted
06 Nov 2019
First published
06 Nov 2019

Org. Chem. Front., 2020,7, 14-18

Metal-free insertion of sulfur dioxide with aryl iodides under ultraviolet irradiation: direct access to sulfonated cyclic compounds

S. Ye, K. Zhou, P. Rojsitthisak and J. Wu, Org. Chem. Front., 2020, 7, 14 DOI: 10.1039/C9QO01274E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements