Synthesis of Alkyl Fluorides by Silver-Catalyzed Radical Decarboxylative Fluorination of Cesium Oxalates

被引:16
|
作者
Vincent, Emilie [1 ]
Brioche, Julien [1 ]
机构
[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA UMR 6014, F-76000 Rouen, France
关键词
Alkyl fluorides; Cesium oxalates; Radical fluorination reactions; Silver catalysis; QUATERNARY CARBON CENTERS; TERTIARY ALCOHOLS; CARBOXYLIC-ACIDS; PHOTOREDOX; DEOXYFLUORINATION; TRIFLUOROMETHYLATION; CONSTRUCTION; FRAGMENTATION; NUCLEOSIDES; GENERATION;
D O I
10.1002/ejoc.202100344
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A combination of silver nitrate (AgNO3) catalyst and Selectfluor (R) was found to perform radical deoxyfluorination of cesium oxalates derived from corresponding alcohols. The reaction tolerates a wide range of functional groups and provides preferentially access to tertiary alkyl fluorides.
引用
收藏
页码:2421 / 2430
页数:10
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