A direct Ni-catalyzed deoxygenative Suzuki-Miyaura cross-coupling reaction of phenols via the formation of active O-phenyluronium

Abstract

Herein, we demonstrate that activation of phenols by tetramethylfluoroformamidinium hexafluorophosphate (TFFH) enables the establishment of the general Ni-catalyzed method for deoxygenative Suzuki-Miyaura cross-coupling reactions of phenols under mild conditions. This Ni-catalyzed method for the deoxygenative transformation of phenols enjoys the broad substrate scope for both coupling partners, and tolerates a great variety of the functional groups some of which are active towards Ni-mediated oxidative addition step, as exhibited by both the transformations of the complex biologically active molecules containing phenol fragments and syntheses of the direct precursors to complex biologically active compounds. Moreover, this Ni-catalyzed method offers a valuable complement to the traditional Suzuki-Miyaura cross-coupling reaction.