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

• DOI: 10.1016/j.tet.2020.131477
• Publication Date: 2020-08-12T01:24:55Z
• Authors: Wei Wang; Pingyang Wang; Qian Zhang; Pengcheng Du; Jianhua Zhang; Hongmei Deng; Haizhen Jiang
• Keywords: Radical-nucleophilic aromatic substitution; Substitution reaction; Intramolecular reaction; Nucleophilic Addition

Abstract A facile and efficient method for construction of S-CF2 or O-CF2 bonds through intermolecular radical nucleophilic substitution (SRN1) reaction of 2-bromo-2,2-difluoro-N-phenylacetamide and thiophenols or phenols was developed, which has also been successfully utilized in the intramolecular SRN1 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.