| Title: |
Hexafluorophosphate-Triggered Hydrogen Isotope Exchange (HIE) in Fluorinated Environments: A Platform for the Deuteration of Aromatic Compounds via Strong Bond Activation |
| Authors: |
Ni, Yang; Lebelt, Jonathan; Barp, Milena; Kreuter, Florian; Buttkus, Hannah; Jin, Jiaye; Kretzschmar, Martin; Tonner-Zech, Ralf; Asmis, Knut R.; Gulder, Tanja |
| Publisher Information: |
Saarländische Universitäts- und Landesbibliothek |
| Publication Year: |
2024 |
| Collection: |
SciDok - Der Wissenschaftsserver der UdS (Universität des Saarlandes) |
| Subject Terms: |
ddc:500; deuterium; 1,1,1,3,3,3-hexafluoroisopropanol; ion vibrational spectroscopy; computational chemistry; hydrogen bonding cluster |
| Description: |
There is a perpetual need for efficient and mild methods to integrate deuterium atoms into carbon frameworks through late-stage modifications. We have developed a simple and highly effective synthetic route for hydrogen isotope exchange (HIE) in aromatic compounds under ambient conditions. This method utilizes catalytic amounts of hexafluorophosphate (PF6 ) in deuterated 1,1,1,3,3,3-hexafluoroisopropanol (HFIPd1) and D2O. Phenols, anilines, anisoles, and heterocyclic compounds were converted with high yields and excellent deuterium incorporations, which allows for the synthesis of a wide range of deuterated aromatic compounds. Spectroscopic and theoretical studies show that an interactive H-bonding network triggered by HFIP-d1 activates the typically inert P F bond in PF6 for D2O addition. The thus in situ formed DPO2F2 then triggers HIE, offering a new way to deuterated building blocks, drugs, and natural-product derivatives with high deuterium incorporation via the activation of strong bonds. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| Relation: |
https://onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fanie.202417889&file=anie202417889-sup-0001-misc_information.pdf; hdl:20.500.11880/39744 |
| DOI: |
10.22028/D291-44535 |
| DOI: |
10.1002/anie.202417889 |
| Availability: |
http://nbn-resolving.org/urn:nbn:de:bsz:291--ds-445351; https://doi.org/10.22028/D291-44535; https://doi.org/10.1002/anie.202417889 |
| Rights: |
openAccess ; Attribution-NonCommercial-NoDerivatives 4.0 International CC BY-NC-ND 4.0 Deed ; https://creativecommons.org/licenses/by-nc-nd/4.0/ |
| Accession Number: |
edsbas.CB13C2A8 |
| Database: |
BASE |