PhenoFluor Solution for Convenient, One-step Deoxyfluorination

The functional-group-tolerant, one-step conversion of phenols to aryl fluorides is a highly desirable process. PhenoFluor™ solution, an innovative reagent developed by Ritter and co-workers,1 provides a straightforward method to fluorinate alcohol and phenols without preactivation and regioselectively fluorinate highly functionalized late-stage intermediates. In collaboration with Tobias Ritter, we now offer two convenient formulation of PhenoFluor™ solution that can be readily used outside of the glovebox.

Phenofluor formulations

General Reaction Scheme

Phenofluor reactions scheme

PhenoFluor™ solution is a thermally stable deoxyfluorinating agent that delivers aryl fluorides from phenols in a one-step, high–yield, ipso substitution reaction. The method is operationally simple, regiospecific, scalable, and compatible with a variety of functional groups including amines, aldehydes, and heterocycles. More recently, it was reported that PhenoFluor™ solution can be used in a late-stage functionalization (LSF) strategy by deoxyfluorinating several natural products and drug-like molecules in a highly regioselective fashion.

Representative Substrate Scope

Representative substrate scope
Materials
Loading

References

1.
Tang P, Wang W, Ritter T. 2011. Deoxyfluorination of Phenols. J. Am. Chem. Soc.. 133(30):11482-11484. http://dx.doi.org/10.1021/ja2048072
2.
Sladojevich F, Arlow SI, Tang P, Ritter T. 2013. Late-Stage Deoxyfluorination of Alcohols with PhenoFluor. J. Am. Chem. Soc.. 135(7):2470-2473. http://dx.doi.org/10.1021/ja3125405
3.
Fujimoto T, Becker F, Ritter T. 2014. PhenoFluor: Practical Synthesis, New Formulation, and Deoxyfluorination of Heteroaromatics. Org. Process Res. Dev.. 18(8):1041-1044. http://dx.doi.org/10.1021/op500121w
4.
Fujimoto T, Ritter T. 2015. ChemInform Abstract: PhenoFluorMix: Practical Chemoselective Deoxyfluorination of Phenols.. ChemInform. 46(25):no-no. http://dx.doi.org/10.1002/chin.201525084

PhenoFluor is a trademark of SciFluor Life Sciences, LLC.

Sure/Seal is a trademark of Merck KGaA, Darmstadt, Germany and/or its affiliates.

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.