SO2F2 mediated click chemistry enables modular disulfide formation in diverse reaction media

Hengzhao Li, Mengqi Peng, Junyu Li, Lijun Wang, Hainam Do, Ke Ni, Minlong Wang, Zhankui Yuan, Tianxiao Zhao, Xiaohe Zhang, Xiaoxu Zhang, Zhaonong Hu, Fazheng Ren and Jie An ()
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Hengzhao Li: China Agricultural University
Mengqi Peng: China Agricultural University
Junyu Li: China Agricultural University
Lijun Wang: China Agricultural University
Hainam Do: University of Nottingham Ningbo China
Ke Ni: China Agricultural University
Minlong Wang: China Agricultural University
Zhankui Yuan: China Agricultural University
Tianxiao Zhao: China Agricultural University
Xiaohe Zhang: China Agricultural University
Xiaoxu Zhang: China Agricultural University
Zhaonong Hu: Northwest A&F University
Fazheng Ren: China Agricultural University
Jie An: China Agricultural University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The dynamic disulfide linkage plays a vital role in various biological processes as well as drugs and biomaterials. The conversion of thiols to their corresponding disulfides is a hallmark of sulfur chemistry, but notoriously difficult to control. Achieving optimal reactivity and selectivity continues to pose significant challenges. Here, we describe a click chemistry for disulfide formation from thiols in both batch and flow-mode using SO2F2, which display exceptional selectivity toward disulfide formation through an effective nucleophilic substitution cascade. This reaction’s unique characteristics satisfy the stringent click-criteria with its high thermodynamic driving force, straightforward conditions, wide scope, quantitative yields, exceptional chemoselectivity, and non-chromatographic purification process. The modular synthesis of symmetrical, unsymmetrical, cyclic and polydisulfides is demonstrated, along with the formation of disulfide cross-linked hydrogels.

Date: 2024
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DOI: 10.1038/s41467-024-52606-w

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