Iodoarene-catalyzed fluorination and aminofluorination by an Ar-I/HF·pyridine/mCPBA system

We have developed the iodoarene-catalyzed nucleophilic fluorination of β-dicarbonyl compounds and intramolecular aminofluorination of ω-amino-alkenes using the same reaction conditions. The key for this reaction is the in situ generation of a hypervalent iodine compound ArIF 2 by hydrogen fluoride,...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2014, Vol.5 (7), p.2754-2760
Main Authors: Suzuki, Satoru, Kamo, Tomohiro, Fukushi, Kazunobu, Hiramatsu, Takaaki, Tokunaga, Etsuko, Dohi, Toshifumi, Kita, Yasuyuki, Shibata, Norio
Format: Article
Language:English
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Summary:We have developed the iodoarene-catalyzed nucleophilic fluorination of β-dicarbonyl compounds and intramolecular aminofluorination of ω-amino-alkenes using the same reaction conditions. The key for this reaction is the in situ generation of a hypervalent iodine compound ArIF 2 by hydrogen fluoride, m CPBA and a catalytic amount of iodoarene. Preliminary trials of catalytic asymmetric nucleophilic fluorination were conducted.
ISSN:2041-6520
2041-6539
DOI:10.1039/C3SC53107D