N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions

A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alka...

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Veröffentlicht in:Advanced synthesis & catalysis 2023-08, Vol.365 (16), p.2744-2750
Hauptverfasser: Kitamura, Tsugio, Kitamura, Daichi, Oyamada, Juzo, Higashi, Masahiro, Kishikawa, Yosuke
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Sprache:eng
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Zusammenfassung:A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alkanes, geminal difluorinated compounds, 2‐fluorinated‐1,3‐dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues of the fluorination reaction using conventional mCPBA as a terminal oxidant but also constructs a simpler catalytic cycle. The present N−F reagent can be recovered as 2,2’‐bipyridine.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300265