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Issue 7, 2014
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Iodoarene-catalyzed fluorination and aminofluorination by an Ar-I/HF·pyridine/mCPBA system

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Abstract

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 ArIF2 by hydrogen fluoride, mCPBA and a catalytic amount of iodoarene. Preliminary trials of catalytic asymmetric nucleophilic fluorination were conducted.

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

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Supplementary files

Article information


Submitted
10 Nov 2013
Accepted
07 Mar 2014
First published
11 Mar 2014

Chem. Sci., 2014,5, 2754-2760
Article type
Edge Article
Author version available

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

S. Suzuki, T. Kamo, K. Fukushi, T. Hiramatsu, E. Tokunaga, T. Dohi, Y. Kita and N. Shibata, Chem. Sci., 2014, 5, 2754
DOI: 10.1039/C3SC53107D

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