Deuterium Exchange between Arenes and Deuterated Solvents in the Absence of a Transition Metal: Synthesis of D-Labeled Fluoroarenes

Abstract

Fluoroarenes can be selectively deuterated by H/D exchange with common deuterated solvents in the presence of a catalytic amount of an alkali metal carbonate or, for the less acidic arenes, stoichiometric quantities of potassium phosphate. This is a sustainable method that does not need transition metal catalysis or the multistep synthesis of a main-group orga- nometallics. This exchange needs to be taken into account when using H/D scrambling as a mechanistic probe in reactions involving fluoroarenes.