Silver-Catalyzed Radical Phosphonofluorination of Unactivated Alkenes

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• 作者：Chengwei Zhang ; Zhaodong Li ; Lin Zhu ; Limei Yu ; Zhentao Wang ; Chaozhong Li
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：September 25, 2013
• 年：2013
• 卷：135
• 期：38
• 页码：14082-14085
• 全文大小：303K
• 年卷期：v.135,no.38(September 25, 2013)
• ISSN：1520-5126

文摘

We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO₃, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH₂Cl₂/H₂O/HOAc at 40 掳C led to the efficient synthesis of 尾-fluorinated alkylphosphonates with good stereoselectivity and wide functional group compatibility. A mechanism involving silver-catalyzed oxidative generation of phosphonyl radicals and silver-assisted fluorine atom transfer is proposed.