Synthesis of Dideuterofluoroarene 3 ΔF(D)-NMR Reporter-Resolvers for Structural, Mechanistic, and Kinetic Studies
Abstract
3,5-Dideutero-4-fluorophenyl compounds are generated by ipso-functionalization of (4-fluorophenyl)trimethylsilane- d 2, prepared in >99 atom % isotopic purity, on a multigram scale, by selective H/D exchange at the C–H sites, ortho to fluorine, using a Lochmann–Schlosser superbase and MeOD. The 3,5-dideutero-4-fluorophenyl “reporter-resolver” system has an isotope shift, Δδ F, in the range of 0.5 to 0.6 ppm. It enables in situ 19 F NMR spectroscopic reaction monitoring of crossover, entrainment, ratiometric heavy atom KIEs, and unambiguous structural assignments and integrations via three NMR-active nuclei.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Molecular Sensors and Ion Detection
Synthesis and properties of polymers
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 14
- Pages
- 5255–5260
- Publication date
- 30 March 2026
- Language
- EN