PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent

Matthew K Nielsen; Christian R Ugaz; Wenping Li; Abigail G Doyle

doi:10.1021/jacs.5b06307

PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent

J Am Chem Soc. 2015 Aug 5;137(30):9571-4. doi: 10.1021/jacs.5b06307. Epub 2015 Jul 21.

Authors

Matthew K Nielsen¹, Christian R Ugaz¹, Wenping Li², Abigail G Doyle¹

Affiliations

¹ †Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
² ‡Department of Imaging Research, Merck Research Laboratories, West Point, Pennsylvania 19486, United States.

PMID: 26177230
DOI: 10.1021/jacs.5b06307

Abstract

We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [(18)F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alcohols / chemistry*
Halogenation
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry
Molecular Structure
Pyridines / chemistry*
Sulfones / chemistry*

Substances

Alcohols
Hydrocarbons, Fluorinated
Pyridines
Sulfones