A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO₂F radical reagent.

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.

SUBMITTER: Zhang W 

PROVIDER: S-EPMC9206656 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature