Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride.
Gemma C Geary1, Eric G Hope, Kuldip Singh
1Department of Chemistry, University of Leicester, Leicester, LE1 7RH, UK. Alison.Stuart@le.ac.uk.
Chemical Communications (Cambridge, England)
|September 3, 2013
Summary
A novel fluoroiodane reagent was synthesized and used for electrophilic fluorination. It efficiently monofluorinates 1,3-ketoesters and difluorinates 1,3-diketones, offering a new tool for organic synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Electrophilic fluorinating reagents are crucial in organic synthesis.
- Development of stable and efficient fluorinating agents is an ongoing area of research.
Purpose of the Study:
- To report the synthesis and application of a new air and moisture stable fluoroiodane reagent.
- To demonstrate its utility in the selective fluorination of carbonyl compounds.
Main Methods:
- Synthesis of fluoroiodane 8 via nucleophilic fluorination of hydroxyiodane 7 using TREAT-HF.
- Application of fluoroiodane 8 as an electrophilic fluorinating agent.
Main Results:
- Fluoroiodane 8 was prepared on a 6 g scale.
- Successful monofluorination of 1,3-ketoesters.
- Successful difluorination of 1,3-diketones.
- Good isolated yields were achieved for both reactions.
Conclusions:
- Fluoroiodane 8 is a stable and effective electrophilic fluorinating reagent.
- This reagent provides a new method for selective fluorination of 1,3-dicarbonyl compounds.
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