Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates

Nature Chemistry
Bing GaoK Barry Sharpless

Abstract

Polysulfates and polysulfonates possess exceptional mechanical properties making them potentially valuable engineering polymers. However, they have been little explored due to a lack of reliable synthetic access. Here we report bifluoride salts (Q+[FHF]-, where Q+ represents a wide range of cations) as powerful catalysts for the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl silyl ethers and aryl fluorosulfates (or alkyl sulfonyl fluorides). The bifluoride salts are significantly more active in catalysing the SuFEx reaction compared to organosuperbases, therefore enabling much lower catalyst-loading (down to 0.05 mol%). Using this chemistry, we are able to prepare polysulfates and polysulfonates with high molecular weight, narrow polydispersity and excellent functional group tolerance. The process is practical with regard to the reduced cost of catalyst, polymer purification and by-product recycling. We have also observed that the process is not sensitive to scale-up, which is essential for its future translation from laboratory research to industrial applications.

References

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Aug 13, 2014·Angewandte Chemie·Jiajia DongK Barry Sharpless

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Citations

Mar 16, 2018·Angewandte Chemie·Digvijay GahtoryHan Zuilhof
Jun 28, 2018·Chemistry : a European Journal·Digvijay GahtoryHan Zuilhof
Aug 17, 2018·Angewandte Chemie·Taha HmissaArsalan Mirjafari
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May 9, 2019·Organic & Biomolecular Chemistry·Jing Leng, Hua-Li Qin
Aug 1, 2019·Chemical Society Reviews·A S BarrowJ E Moses
Sep 6, 2019·Proceedings of the National Academy of Sciences of the United States of America·Qinheng ZhengK Barry Sharpless
Jan 31, 2020·Chemistry : a European Journal·Jitendra Gurjar, Valery V Fokin
Aug 23, 2019·Nature Communications·Ruting XuSaihu Liao
May 8, 2020·Chemistry : a European Journal·Sebastian Hasenstab-RiedelJulia Bader
Nov 27, 2019·Nature Chemical Biology·Heung Sik HahmKu-Lung Hsu
Aug 31, 2019·Beilstein Journal of Organic Chemistry·Jing LiuHua-Li Qin
Sep 30, 2020·Macromolecular Rapid Communications·Tieshuai ZhaoCaglar Remzi Becer
Nov 17, 2020·Angewandte Chemie·Xingliang NieSaihu Liao
Feb 26, 2021·Journal of the American Chemical Society·Qinheng ZhengPeng Wu
Mar 5, 2021·Chemical Reviews·Bauke AlbadaFloris van Delft
Jun 8, 2021·Chemical Science·Ryan W KulowQuentin Michaudel
Jun 8, 2021·RSC Chemical Biology·Adam L BorneKu-Lung Hsu
Jun 24, 2021·Organic Letters·Shuheng Xu, Sunliang Cui
Jun 24, 2021·Organic & Biomolecular Chemistry·Zai-Wei ZhangHaolin Tang
Jun 15, 2021·ACS Catalysis·Cayo LeeNicholas D Ball
Jul 11, 2021·Proceedings of the National Academy of Sciences of the United States of America·Jiong ZhangK Barry Sharpless
Jul 29, 2021·Chemical Communications : Chem Comm·Xiu WangJinbo Hu
Aug 6, 2021·Chemical Science·Tao ZhongJiang Weng
Apr 25, 2020·Journal of the American Chemical Society·Jeffrey W BruletKu-Lung Hsu

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