Construction of S-CF2/ O-CF2 bonds via inter/intramolecular radical nucleophilic substitution reaction

Article abstract of DOI:10.1016/j.tet.2020.131477

A facile and efficient method for construction of S-CF₂ or O-CF₂ bonds through intermolecular radical nucleophilic substitution (S_RN1) reaction of 2-bromo-2,2-difluoro-N-phenylacetamide and thiophenols or phenols was developed, which has also been successfully utilized in the intramolecular S_RN1 reaction to generate a new O-CF₂ bonds for synthesis of biologically important 2,2-difluoro-2H-benzo [1,4]oxazin-3-one. The protocol enables an efficient access to gem-difluoromethylene-containing thioethers or ethers and oxazin heterocycles with good to excellent yields by inter/intramolecular radical nucleophilic substitution reaction under mild reaction conditions.