Synthesis of stable α-fluoromethyl putative carbanions via a chemoselective reduction-monofluoromethylation sequence of diselenides under sustainable conditions. (9th April 2021)

• Record Type: Journal Article
• Authors: Senatore, Raffaele; Malik, Monika; Urban, Ernst; Holzer, Wolfgang; Pace, Vittorio
• Is Part Of: Tetrahedron. Volume 85(2021)
• Publication Date: 2021-04-09
• Subjects: Fluorine -- Organoselenium -- Green solvents -- Organometallics -- C1 synthons; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.131921
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: α-Fluoromethyl selenoethers were prepared through a sequential one-pot diselenide reduction-fluoromethylation with the fluorinated, highly manipulable C1 source ICH2 F. The reaction benefited from the employment of the environmentally friendly solvent MeTHF (2-methyltetrahydrofuran) which enabled to maximize the efficiency of both steps of the technique. A series of variously functionalized analogues – featuring a remarkable degree of stability imparted by selenium - could be chemoselectively accessed in high yield and purity through an intuitive and experimentally simple protocol. Graphical abstract: Image 1