Directed Iridium-Catalyzed Hydrogen Isotope Exchange Reactions of Phenylacetic Acid Esters and Amides.
Mégane ValeroDaniel BeckerKristof JessRemo WeckJens AtzrodtThomas BannenbergVolker DerdauMatthias TammPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2019)
For the first time, a catalytic protocol for a highly selective hydrogen isotope exchange (HIE) of phenylacetic acid esters and amides under very mild reaction conditions is reported. Using a homogeneous iridium catalyst supported by a bidentate phosphine-imidazolin-2-imine P,N ligand, the HIE reaction on a series of phenylacetic acid derivatives proceeds with high yields, high selectivity, and with deuterium incorporation up to 99 %. The method is fully adaptable to the specific requirements of tritium chemistry, and its effectiveness was demonstrated by direct tritium labeling of the fungicide benalaxyl and the drug camylofine. Further insights into the mechanism of the HIE reaction with catalyst 1 have been provided utilizing DFT calculations, NMR studies, and X-ray diffraction analysis.
Keyphrases
- room temperature
- randomized controlled trial
- visible light
- high resolution
- density functional theory
- ionic liquid
- systematic review
- magnetic resonance
- highly efficient
- crystal structure
- emergency department
- carbon dioxide
- molecular dynamics simulations
- molecular docking
- magnetic resonance imaging
- mass spectrometry
- gas chromatography
- electron transfer
- gold nanoparticles
- case control
- solid state
- structure activity relationship