Synthesis of Unsymmetrical α,α-Diarylacetates

Ethyl bromofluoroacetate has been developed as a precursor for the convenient synthesis of unsymmetrical alpha,alpha-diarylacetates featuring indoles, anilines, and other electron-rich aromatics. In conjunction with a mild Lewis acid catalyzed C-N -> C-C exchange, intermediate arylglycines can be synthesized and transformed into alpha,alpha a-diarylacetates in a one-pot protocol, resulting in a net diarylation reaction exhibiting a wide scope. In the context of diarylacetates, the synthetic equivalence of the fluorinated reagent with a-nitro-a-diazo carbonyls was established.