PhenoFluorMix: practical chemoselective deoxyfluorination of phenols
Teppei Fujimoto1, Tobias Ritter
1Department of Chemistry and Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
Organic Letters
|January 27, 2015
Summary
A new reagent, PhenoFluorMix, offers a stable and practical method for deoxyfluorination. This air-stable mixture effectively converts phenols and heterocycles into their fluorinated counterparts without hydrolysis issues.
Area of Science:
- Organic Chemistry
- Fluorination Chemistry
Background:
- Deoxyfluorination is a crucial transformation in organic synthesis.
- Existing deoxyfluorinating reagents often suffer from hydrolysis and limited stability.
- PhenoFluor is a known reagent but susceptible to hydrolysis, limiting its practical application.
Purpose of the Study:
- To introduce a novel, stable, and practical deoxyfluorinating reagent, PhenoFluorMix.
- To demonstrate the utility of PhenoFluorMix in the deoxyfluorination of various organic substrates.
- To overcome the hydrolysis limitations associated with previous reagents.
Main Methods:
- PhenoFluorMix was prepared as a mixture of N,N'-1,3-bis(2,6-diisopropylphenyl)chloroimidazolium chloride and CsF.
- The stability of PhenoFluorMix towards hydrolysis was assessed.
- The deoxyfluorination of a diverse range of phenols and heterocycles using PhenoFluorMix was performed and analyzed.
Main Results:
- PhenoFluorMix demonstrated excellent stability and resistance to hydrolysis.
- The reagent is readily available on a decagram scale and can be stored in air.
- Successful deoxyfluorination of various phenols and heterocyclic compounds was achieved using PhenoFluorMix.
Conclusions:
- PhenoFluorMix represents a practical and robust advancement in deoxyfluorination methodology.
- The reagent's stability and ease of handling make it a valuable tool for synthetic chemists.
- This method provides an efficient route to fluorinated phenols and heterocycles.
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