Synthesis of Polyfluoroalkyl Aryl Ethers Mediated by Sulfuryl Fluoride as a Traceless Activator
Year: 2024
Type: article
Abstract: 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 2 F 2 ). 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.
Source: Organic Letters
Institutions: Centre National de la Recherche Scientifique, Université de Haute-Alsace, Laboratoire d'innovation moléculaire et applications, Université de Strasbourg, Sorbonne Université, Laboratoire de Chimie Théorique, Normandie Université, Laboratoire COBRA, Institut National des Sciences Appliquées Rouen Normandie, Bayer (France), Bayer (Germany)
Language: English
Subfield: Pharmaceutical Science
Domain: Life Sciences
Open Access status: green
OpenAlex ID: W4404246098