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- Title
A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO<sub>2</sub>F radical reagent.
- Authors
Zhang, Weigang; Li, Heyin; Li, Xiaojuan; Zou, Zhenlei; Huang, Mengjun; Liu, Jiyang; Wang, Xiaochen; Ni, Shengyang; Pan, Yi; Wang, Yi
- Abstract
Sulfonyl fluorides are key components in the fields of chemical biology, materials science and drug discovery. In this line, the highly active SO2F radical has been employed for the construction of sulfonyl fluorides, but the utilization of gaseous ClSO2F as radical precursor is limited due to the tedious and hazardous preparation. Meanwhile, the synthesis of sulfonyl fluorides from inert SO2F2 gas through a fluorosulfonyl radical (·SO2F) process has met with inevitable difficulties due to the high homolytic bond dissociation energy of the S(VI)-F bond. Here we report a radical fluorosulfonylation strategy for the stereoselective synthesis of alkenyl sulfonyl fluorides and functional alkyl sulfonyl fluorides with an air-stable crystalline benzimidazolium fluorosulfonate cationic salt reagent. This bench-stable redox-active reagent offers a useful and operational protocol for the radical fluorosulfonylation of unsaturated hydrocarbons with good yield and high stereoselectivity, which can be further transformed into valuable functional SO2F moieties. Sulfonyl fluorides have potential application in chemical biology, materials science, and drug discovery, but their preparation remains challenging. Here, the authors report an air-stable fluorosulfonylating reagent that enables the radical fluorosulfonylation, hydrofluorosulfonylation and migratory SO2F-difunctionalization of unsaturated hydrocarbons to construct a variety of sulfonyl fluoride compounds.
- Subjects
DRUG discovery; CHEMICAL biology; SULFONYL compounds; MATERIALS science; ALKENYL group; CHEMICAL potential
- Publication
Nature Communications, 2022, Vol 13, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-022-31296-2