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 (SO2F2). Polyfluoroalkyl aryl ethers are present in a variety of biologically active compounds, but previous methods for a...

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Bibliographic Details
Published in:Organic letters 2024-11, Vol.26 (46), p.10046-10050
Main Authors: Plaçais, Clotilde, Wisson, Lilian, Chataigner, Isabelle, Donnard, Morgan, Panossian, Armen, Vors, Jean-Pierre, Bernier, David, Pazenok, Sergii, Leroux, Frédéric R.
Format: Article
Language:English
Subjects:
Chemical Sciences
heterocyclic compounds
Lewis acids
Lewis bases
Organic chemistry
sulfuryl fluoride
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Summary: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 (SO2F2). 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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03989