Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry,Chemical Science

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Synthesis of unsymmetrical sulfamides and polysulfamides via SuFEx click chemistry
Chemical Science ( IF 7.6 ) Pub Date : 2020-07-13 , DOI: 10.1039/d0sc03606d
Ryan W. Kulow _{1,

2,

3,

4} , Jiun Wei Wu _{1,

2,

3,

4} , Cheoljae Kim _{1,

2,

3,

4} , Quentin Michaudel _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

通过SuFEx点击化学合成不对称的磺酰胺和多磺酰胺

作为氢键供体和受体，N，N′-二取代的硫酰胺已用于从药物化学到阴离子结合催化的一系列应用中。然而，与脲或硫脲相比，该独特部分的利用仍然是微不足道的，部分原因是缺乏通用的合成方法来获得不对称的磺酰胺。具体地说，尽管聚磺酰胺在非共价动态网络中具有潜在的实用性，但实际上却是一种未知类型的聚合物，这是材料科学领域的一个重要研究领域。我们在此报告一种实用而有效的方法制备硫酰胺不对称经由硫（VI）-氟化物交换（SuFEx）单击化学。然后将该方法应用于合成聚磺酰胺。热分析表明，该系列聚合物具有很高的热稳定性和可调节的玻璃化转变温度。最后，水解研究表明，芳香族聚磺酰胺可在其生命周期结束时再循环回其组成单体。

更新日期：2020-08-05

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