Copper-Mediated Oxidative Chloro- and Bromodifluoromethylation of Phenols

Abstract

The first oxidative chloro- and bromodifluoromethylation of phenols with (CH3)3SiCF2X and CuX (X = Cl or Br) in the presence of Selectfluor under mild reaction conditions was developed. This protocol provided a practical and efficient method for the synthesis of a diverse range of biologically valuable and synthetically challenging chloro- and bromodifluoromethyl aryl ethers. Preliminary mechanistic studies suggest that this reaction proceeded through a difluorocarbene-involved oxidative coupling process.

Three-component approach to modular synthesis of tetra-substituted furans and pyrroles

“…1 Using TMSCF 2 Br as a difluorocarbene precursor or a trimethylsilyldifluoromethyl radical precursor, a broad spectrum of fluoro-containing compounds has been constructed in high efficiency (Scheme 1a). 2 Additionally, the exploration of novel chemical reactivities of readily available feedstocks has always been a hot topic in the synthetic arena. 3 Such exploration can not only tap the potential of these chemical reagents but also open new doors for the preparation of various high-value-added products.…”