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Silver-Catalyzed Decarboxylative Fluorination of Aliphatic Carboxylic Acids in Aqueous Solution

2012; American Chemical Society; Volume: 134; Issue: 25 Linguagem: Inglês

10.1021/ja3048255

1943-2984

Feng Yin, Zhentao Wang, Zhaodong Li, Chaozhong Li,

Radical Photochemical Reactions

Although fluorinated compounds have found widespread applications in the chemical and materials industries, general and site-specific C(sp(3))-F bond formations are still a challenging task. We report here that with the catalysis of AgNO(3), various aliphatic carboxylic acids undergo efficient decarboxylative fluorination with SELECTFLUOR(®) reagent in aqueous solution, leading to the synthesis of the corresponding alkyl fluorides in satisfactory yields under mild conditions. This radical fluorination method is not only efficient and general but also chemoselective and functional-group-compatible, thus making it highly practical in the synthesis of fluorinated molecules. A mechanism involvinig Ag(III)-mediated single electron transfer followed by fluorine atom transfer is proposed for this catalytic fluorodecarboxylation.