Research News

Scientists develop a new method to incorporate harmful perfluoroalkenes into N-heterocyclic carbene ligands

Converting PFAS “forever chemicals” into valuable carbenes

The conversion was achieved by simply removing two fluorine atoms from 1,2-difluoroalkene derivatives

Osaka, Japan – Commonly known as “forever chemicals,” PFAS are notorious for persisting in the environment and in our bodies. Osaka Metropolitan University chemists may put an end to the “forever” life of PFAS with their simple yet innovative technique that converts these harmful substances into valuable compounds.

A research group led by Professor Masato Ohashi and Assistant Professor Kenichi Michigami of the Graduate School of Science at Osaka Metropolitan University has successfully synthesized ligands called fluorine-decorated N-heterocyclic carbenes (NHCs) from perfluoroalkenes, a type of PFAS (Perfluoroalkyl and Polyfluoroalkyl Substances). The NHCs developed in this study play significant roles in stabilizing unstable molecules as well as enhancing the performance of their ligated transition metal complexes.

The synthesis of fluorinated NHCs was achieved simply by removing two fluorine atoms from 1,2-difluoroalkene derivatives. Owing to the small size of fluorine atoms, the electron-accepting ability of the NHC ligand can be enhanced without substantially changing its steric properties.

“Our results enable the easy transformation of harmful PFAS into functional NHCs,” explained Dr. Michigami. “The versatile applications of fluorinated NHCs show potential advantages in various fields such as fluorine chemistry, organometallic chemistry, catalysis chemistry, and materials science.”

Their findings were published in the Journal of the American Chemical Society.

Funding

This work was supported by Grants-in-Aid for Scientific Research (B) (JSPS KAKENHI grants 16KT0057, 17H03057, and 23H01964) and for Young Scientists (JSPS KAKENHI grant JP21K14632). We also appreciate the financial support by the Leading Initiative for Excellent Young Researchers, MEXT, Japan.

Paper Information

Journal: Journal of the American Chemical Society
Title: N-Heterocyclic Carbenes with Polyfluorinated Groups at the 4- and 5-Positions from [3 + 2] Cycloadditions between Formamidinates and cis-1,2-Difluoroalkene Derivatives
DOI: 10.1021/jacs.3c06331
Author: Masato Ohashi, Kota Ando, Shoichi Murakami, Kenichi Michigami, Sensuke Ogoshi
Published: September 26, 2023

https://pubs.acs.org/doi/full/10.1021/jacs.3c06331

Contact

Graduate School of Science
Kenichi Michigami
E-mail: kn1michigami[at]omu.ac.jp

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