A direct Ni-catalyzed deoxygenative Suzuki-Miyaura cross-coupling reaction of phenols via the formation of active O-phenyluronium
Year: 2024
Type: article
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. Herein, we demonstrate a mild deoxygenative synthesis of diversified biaryl motifs directly from regenerable and low-toxic phenols, thereby preventing the utilization of lengthily multistep synthesized aryl halides from producing redundant wastes. Notably, the general activator TFFH for acids was unveiled as a powerful activator for the phenolic C ( sp 2 )-O bond via O -phenyluronium by its strong oxophilicity.
Source: Green Synthesis and Catalysis
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4404353497