α-Fluoromethyl selenoethers were prepared through a sequential one-pot diselenide reduction-fluoromethylation with the fluorinated, highly manipulable C1 source ICH2F. 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.
Synthesis of stable α-fluoromethyl putative carbanions via a chemoselective reduction-monofluoromethylation sequence of diselenides under sustainable conditions
Pace V.
Last
2021-01-01
Abstract
α-Fluoromethyl selenoethers were prepared through a sequential one-pot diselenide reduction-fluoromethylation with the fluorinated, highly manipulable C1 source ICH2F. 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.
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