Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts

We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]­octane-bis­(sulfur dioxide) adduct as a convenient sulfonyl source in combinat...

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Veröffentlicht in:Organic letters 2020-03, Vol.22 (6), p.2281-2286
Hauptverfasser: Liu, Yongan, Yu, Donghai, Guo, Yong, Xiao, Ji-Chang, Chen, Qing-Yun, Liu, Chao
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Sprache:eng
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Zusammenfassung:We report herein a general and practical copper-catalyzed fluorosulfonylation reaction of a wide range of abundant arenediazonium salts to smoothly prepare various arenesulfonyl fluorides using the 1,4-diazabicyclo[2.2.2]­octane-bis­(sulfur dioxide) adduct as a convenient sulfonyl source in combination with KHF2 as an ideal fluorine source and without the need for additional oxidants. Interestingly, the electronic character of the arene ring in the starting arenediazonium salts has a significant impact on the reaction mechanistic pathway.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00484