Issue 30, 2020

Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry

Abstract

As hydrogen-bond donors and acceptors, N,N′-disubstituted sulfamides have been used in a range of applications from medicinal chemistry to anion-binding catalysis. However, compared to ureas or thioureas, the utilization of this unique moiety remains marginal, in part because of a lack of general synthetic methods to access unsymmetrical sulfamides. Specifically, polysulfamides are a virtually unknown type of polymer despite their potential utility in non-covalent dynamic networks, an intense area of research in materials science. We report herein a practical and efficient process to prepare unsymmetrical sulfamides via Sulfur(VI)-Fluoride Exchange (SuFEx) click chemistry. This process was then applied to synthesize polysulfamides. Thermal analysis showed that this family of polymers possess high thermal stability and tunable glass transition temperatures. Finally, hydrolysis studies indicated that aromatic polysulfamides could be recycled back to their constituting monomers at the end of their life cycle.

Graphical abstract: Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry

Supplementary files

Article information

Article type
Edge Article
Submitted
01 jul 2020
Accepted
10 jul 2020
First published
13 jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 7807-7812

Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry

R. W. Kulow, J. W. Wu, C. Kim and Q. Michaudel, Chem. Sci., 2020, 11, 7807 DOI: 10.1039/D0SC03606D

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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