SO<sub>2</sub>F<sub>2</sub> mediated click chemistry enables modular disulfide formation in diverse reaction media.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 39333088.
- Also identified by DOI 10.1038/s41467-024-52606-w and PMC identifier 11436863.
- Licence recorded as CC BY-NC-ND.
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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 SO<sub>2</sub>F<sub>2</sub>, 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.