C−F Arylation of Polyfluorophenols by Means of Sigmatropic Dearomatization/Defluorination Sequence

Abstract

Selective C−F arylation of polyfluorophenols with aryl sulfoxides has been accomplished by means of a sigmatropic dearomatization/defluorination sequence. This sequence consists of three processes: 1) interrupted Pummerer reaction to form S−O‐tethered sulfonium salt; 2) C−C‐forming [3, 3] sigmatropic rearrangement with dearomatization; and 3) Zn‐mediated defluorinative rearomatization. The present biaryl construction provides a facile access to polyfluorinated biaryls that is difficult to synthesize by other methods. The synthetic utility of the strategy is clearly demonstrated by the synthesis of a fluorinated analogue of Maxipost, a potassium channel modulator.