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Deuterium Exchange between Arenes and Deuterated Solvents in the Absence of a Transition Metal: Synthesis of D‐Labeled Fluoroarenes
Author(s) -
Salamanca Vanesa,
Albéniz Ana C.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000284
Subject(s) - chemistry , catalysis , transition metal , deuterium , hydrogen–deuterium exchange , inorganic chemistry , alkali metal , stoichiometry , potassium carbonate , organic chemistry , hydrogen , physics , quantum mechanics
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 organometallics. This exchange needs to be taken into account when using H/D scrambling as a mechanistic probe in reactions involving fluoroarenes.