Issue 5, 2016

Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides

Abstract

A catalyst-free aminosulfonylation through insertion of sulfur dioxide with aryl/alkyl halides enabled by photoenergy is presented. Under ultraviolet irradiation, a three-component reaction of aryl/alkyl halides, sulfur dioxide, and hydrazines proceeds smoothly under mild conditions without any metals or photo-redox catalysts. The corresponding N-aminosulfonamides are afforded in good to excellent yields. A broad reaction scope is demonstrated with good functional group tolerance. Not only aryl bromide but also aryl chloride is suitable under the conditions. Additionally, alkyl halides are good substrates as well during the insertion of sulfur dioxide. A possible mechanism involving a radical process is proposed, supported by theoretical calculations.

Graphical abstract: Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides

Supplementary files

Article information

Article type
Research Article
Submitted
06 feb 2016
Accepted
03 mar 2016
First published
03 mar 2016

Org. Chem. Front., 2016,3, 574-578

Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides

Y. Li, D. Zheng, Z. Li and J. Wu, Org. Chem. Front., 2016, 3, 574 DOI: 10.1039/C6QO00060F

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