Electroreductive hydroxy fluorosulfonylation of alkenes

Qingyuan Feng, Tianyu He, Shencheng Qian, Peng Xu, Saihu Liao and Shenlin Huang ()
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Qingyuan Feng: Nanjing Forestry University
Tianyu He: Nanjing Forestry University
Shencheng Qian: Nanjing Forestry University
Peng Xu: Nanjing Forestry University
Saihu Liao: Xiamen University
Shenlin Huang: Nanjing Forestry University

Nature Communications, 2023, vol. 14, issue 1, 1-8

Abstract: Abstract An electroreductive strategy for radical hydroxyl fluorosulfonylation of alkenes with sulfuryl chlorofluoride and molecular oxygen from air is described. This mild protocol displays excellent functional group compatibility, broad scope, and good scalability, providing convenient access to diverse β-hydroxy sulfonyl fluorides. These β-hydroxy sulfonyl fluoride products can be further converted to valuable aliphatic sulfonyl fluorides, β-keto sulfonyl fluorides, and β-alkenyl sulfonyl fluorides. Further, some of these products showed excellent inhibitory activity against Botrytis cinerea or Bursaphelenchus xylophilus, which could be useful for potent agrochemical discovery. Preliminary mechanistic studies indicate that this transformation is achieved through rapid O2 interception by the alkyl radical and subsequent reduction of the peroxy radical, which outcompete other side reactions such as chlorine atom transfer, hydrogen atom transfer, and Russell fragmentation.

Date: 2023
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DOI: 10.1038/s41467-023-44029-w

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