Synthesis of Functionalized Aliphatic Acid Esters via the Generation of Alkyl Radicals from Silylperoxyacetals

We describe a catalytic method for the synthesis of a variety of functionalized aliphatic acid esters using silylperoxyacetals, which are versatile alkyl radical precursors with a terminal ester moiety. In the presence of an appropriate transition-metal catalyst, the in situ generation of alkyl radicals and the subsequent bond-forming process proceeds smoothly to afford synthetically valuable aliphatic acid derivatives. The present method can be applied to the efficient synthesis of a pharmaceutically important 1,1-diarylalkane motif. In addition, a novel strategy for the synthesis of structurally diverse hydroxy acid derivatives via a C-O bond formation process that utilizes TEMPO has been developed.

Automated summary

A catalytic method for the synthesis of functionalized aliphatic acid esters using silylperoxyacetals has been developed, leading to the efficient synthesis of pharmaceutically important compounds and structurally diverse hydroxy acid derivatives via a C-O bond formation process utilizing TEMPO.