N-Ethyl-N-isopropylpropan-2-aminium 4-oxo-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate is a fluoroarylated-Meldrum′s acid adduct. It can be prepared by reacting pentafluoropyridine with cyclohexyl-Meldrum′s acid in the presence ofN,N-diisopropylethylamine and acetonitrile.This compound undergoes cycloreversion to form the fluoro(hetero)aryl ketene, which undergoes efficient coupling with nucleophiles and allows rapid incorporation of highly fluorinated α-fluoro(hetero)aryl acetic acid derivatives.N-Ethyl-N-isopropylpropan-2-aminium 4-oxo-3-(perfluoropyridin-4-yl)-1,5-dioxaspiro[5.5]undec-2-en-2-olate may be used to synthesize ethyl 2-(2-(perfluoropyridin-4-yl)acetamido)-acetate andN-methoxy-N-methyl-2-(perfluoropyridin-4-yl)-acetamide.
1.Sameera M Senaweera, Jimmie D Weaver,. (2014-10-02) Selective perfluoro- and polyfluoroarylation of Meldrum's acid.. The Journal of organic chemistry, 79 ((21)):( 10466-10476 ). [PMID:25271542]
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