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

Weigang Zhang, Heyin Li, Xiaojuan Li, Zhenlei Zou, Mengjun Huang, Jiyang Liu, Xiaochen Wang, Shengyang Ni, Yi Pan and Yi Wang ()
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Weigang Zhang: Nanjing University
Heyin Li: Nanjing University
Xiaojuan Li: Nanjing University
Zhenlei Zou: Nanjing University
Mengjun Huang: Nanjing University
Jiyang Liu: Nanjing University
Xiaochen Wang: Nanjing University
Shengyang Ni: Nanjing University
Yi Pan: Nanjing University
Yi Wang: Nanjing University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-31296-2

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