Rational Design and Development of Low-Price,Scalable,Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

• 作者: Yafei Liu Yijing Ling Hangming Ge Long Lu Qilong Shen
• 来源期刊: 中国化学（英文版）
• 年，卷（期）: 2021,（6）
• 所属期刊栏目: Comprehensive Reports
• 页码范围: 1667-1682
• 页数: 16页
• 语种: 英文
• DOI: 10.1002/cjoc.202100107

摘要

Main observation and conclusion The development of two highly reactive electrophilic trifluoromethylating reagents(trifluoromethyl)(4-nitrophenyl)bis(carbometh-oxy)methylide(1g)and(trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide(1j)through structure-activity study was de-scribed.Under mild conditions,reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields.In addition,reagent 1g could serve as a trifluoromethyl radical for a variety of trifluo-romethylative transformations under visible light irradiation,including radical trifluoromethylation of electron-rich indoles and pyr-roles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives.On the other hand,as a complimentary,under reductive coupling conditions,reagent 1j reacted with a variety of(hetero)aryl iodides for the formation of tri-fluoromethylated(hetero)arenes.