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Construction of S-CF2/ O-CF2 bonds via inter/intramolecular radical nucleophilic substitution reaction
Tetrahedron ( IF 2.1 ) Pub Date : 2020-08-12 , DOI: 10.1016/j.tet.2020.131477
Wei Wang , Pingyang Wang , Qian Zhang , Pengcheng Du , Jianhua Zhang , Hongmei Deng , Haizhen Jiang

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.



中文翻译:

通过分子间/分子间自由基亲核取代反应构建S-CF 2 / O-CF 2

开发了一种通过2-溴-2,2-二氟-N-苯基乙酰胺与硫酚或酚的分子间自由基亲核取代(S RN 1)反应构建S-CF 2或O-CF 2键的简便有效方法,它也已成功地用于分子内S RN 1反应中,以生成新的O-CF 2键,用于合成生物学上重要的2,2-二氟-2H-苯并[1,4]恶嗪-3-酮。该协议可以有效访问gem在温和的反应条件下,通过分子间/分子间自由基亲核取代反应,具有良好的优良产率的含-二氟亚甲基的硫醚或醚和恶嗪杂环。

更新日期:2020-08-28
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