Facile and Selective Perfluoro- and Polyfluoroarylation of Meldrums Acid

Abstract

This disclosure relates generally to the facile and selective mono-perfluoro and -polyfluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated alpha-phenyl acetic acid derivatives which provide straightforward access to fluorinated building blocks. The reaction takes place quickly and all products were isolated without the need for chromatography. An embodiment provides an alternative strategy to access alpha-arylated Meldrum's acids which avoids the need for aryl-Pb(IV) salts or diaryliodonium salts and provides access to the tertiary product which was not previously synthetically accessible. The synthetic versatility and utility of the Meldrum's acid products is demonstrated by subjecting the products to several derivatizations of the Meldrum's acid products as well as photocatalytic hydrodefluorination which provide access to difficult but valuable synthetic targets such as multifluorinated aromatics.