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Deoxyfluorination of Phenols

Pingping Tang, Weike Wang and Tobias Ritter*

*Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, United States, Email: ritterchemistry.harvard.edu

P. Tang, W. Wang, T. Ritter, J. Am. Chem. Soc., 2011, 133, 11482-11484.

DOI: 10.1021/ja2048072 (free Supporting Information)


Abstract

An operationally simple ipso fluorination of phenols with a new deoxyfluorination reagent can be used conveniently from miligram to multigram scale. Whereas hydrogen bonding is undesirable on conventional nucleophilic fluorination chemistry because it reduces the nucleophilicity of fluoride, hydrogen bonding appears to be crucial for this fluorination method.


see article for more examples



PhenoFluorMix: Practical Chemoselective Deoxyfluorination of Phenols

T. Fujimoto, T. Ritter, Org. Lett., 2015, 17, 544-547.


Key Words

fluoroarenes


ID: J48-Y2011-2150