| Fluorine compounds have been widely used in pharmaceuticals, pesticides, paints and materials because of their unique biological activity and physicochemical properties. Fluorine organic compounds, especially α-fluorinated carbonyl compounds, related to a variety of blockbuster drugs with outstanding efficacy and biological activity, have been selling in the clinical market for many years. In the meantime, α-fluoro carbonyl compounds are also important intermediates in organic synthesis, by which many kinds of fluorine compounds can be synthesized. Thanks to the introduction of fluorine atom to α-position of carbonyl compounds, the physicochemical properties and biological activity of molecules can be greatly improved. Therefore, it is very significant to develop the research of α-fluorinated carbonyl compounds.In this paper, the synthesis and applications α-fluoro-α-ester carbonyl compounds (α-fluoro-β-carbonyl esters were named α-fluoro-α-ester carbonyl compounds to emphasize the use of ester as a general substituted group) and α-fluoro-α-bromo carbonyl compounds were investigated. α-Fluoro-α-ester carbonyl compounds were used to synthesize a series of 3,5-diphenylphenol. The first was the fluorination of ethyl 3-oxobutanoate by SelectfluorTM. Then, the phenol was synthesized by ethyl 2-fluoro-3-oxobutanoate and chalcone via Robinson annulation and aromatization. After the last step, decarboxylation,10 kinds of 3,5-diphenylphenol series compounds were obtained. The difficulties of synthesizing these products were greatly reduced by using this method. What’s more, the overall yields reached to 75～92% after a modified one-pot-two-steps method.14 kinds of α-fluoro-α-bromo carbonyl compounds were synthesized with 63～97% overall yields via bromination by N-bromosuccinimide (NBS) and fluorination by SelectfluorTM. Then,30 kinds of α-fluoro-α-alkoxy carbonyl compounds were synthesized with 60～89% yields via nucleophilic substitution in base by alcohols. |
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