Synthesis of Polyfluoroalkyl Aryl Ethers Mediated by Sulfuryl Fluoride as a Traceless Activator
Herein, we report the metal-free synthesis of polyfluoroalkyl aryl ethers via nucleophilic substitution of fluorosulfonates, obtained in one pot by bubbling of sulfuryl fluoride (SO<sub>2</sub>F<sub>2</sub>). Polyfluoroalkyl aryl ethers are present in a variety of biologically active compounds, but previous methods for accessing them required metal catalysts or harsh conditions. With this method, their synthesis is possible under mild conditions and with a short reaction time (30 min) from commercially available starting materials and in yields of ≤97%. Various fluorinated alcohols could be used as electrophiles, and a diversity of electron-withdrawing groups on the aryl or heteroaryl group were tolerated.
Authors
- Isabelle Chataigner (ORCID: https://orcid.org/0000-0001-6302-7831)
- Morgan Donnard (ORCID: https://orcid.org/0000-0002-9303-4634)
- Clotilde Plaçais
- Frédéric R. Leroux (ORCID: https://orcid.org/0000-0001-8900-5753)
- Lilian Wisson (ORCID: https://orcid.org/0000-0001-7802-7578)
- David Bernier (ORCID: https://orcid.org/0000-0002-3867-6503)
- Sergii Pazenok
- Armen Panossian (ORCID: https://orcid.org/0000-0003-2317-1200)
- Jean-Pierre Vors
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université de Haute-Alsace (FR)
- Sorbonne Université (FR)
- Laboratoire de Chimie Théorique (FR)
- Normandie Université (FR)
- Laboratoire COBRA (FR)
- Bayer (France) (FR)
- Université de Rouen Normandie (FR)
- Bayer (Germany) (DE)
- Université de Strasbourg (FR)
- Institut National des Sciences Appliquées Rouen Normandie (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-11
- DOI
- https://doi.org/10.1021/acs.orglett.4c03989
- Citations
- 4
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.83
Funders
- Université de Strasbourg
- Centre National de la Recherche Scientifique