Perfluoroalkyl Selenoxides, Selenones and Selenoximines: General Preparation and Properties. (10th February 2023)

• Record Type: Journal Article
• Authors: de Zordo‐Banliat, Arnaud; Grollier, Kevin; Vanthuyne, Nicolas; Floquet, Sébastien; Billard, Thierry; Dagousset, Guillaume; Pégot, Bruce; Magnier, Emmanuel
• Is Part Of: Angewandte Chemie. Volume 135:Number 12(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-02-10
• Subjects: Fluorine -- Oxidation -- Selenium -- Selenones -- Selenoximines; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202300951
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A selective access to perfluoroalkyl selenoxides, via Oxone® as oxidant or to selenones by using a Polyoxometalate‐based Ionic Liquid (POM‐IL) as a catalyst for the oxidation step is described. The reaction works with various perfluoralkyl chains and substituents with satisfactory to excellent yields. A two‐step one‐pot reaction from selenocyanates was performed to gain access to perfluoroalkyl selenoxides. The previously unknown perfluoroalkyl selenoximines family was also prepared with good yields. Having unlocked two strategies for the synthesis of fluoroalkylated Se IV and Se VI compounds, we then evaluated the Hansch‐Leo lipophilicity parameters of these groups. Finally, asymmetric aryl perfluoroalkyl selenoximines were resolved to determine their absolute configurations. Abstract : Access to perfluoroalkyl selenoxides, selenones and selenoximines was possible through a selective oxidation of perfluoroalkyl selenoethers. Synthesis of perfluoroalkyl selenoxides was also described via a two‐step one‐pot reaction from selenocyanates. The perfluoroalkyl selenoximine family was synthesized. The Hansch‐Leo parameters of the compounds were determined and some aryl perfluoroalkyl selenoxides were separated by chiral HPLC.