α-Arylation of saturated fatty acids

In this study, we take advantage of the -CH-acidity of fatty acid esters in order to obtain -arylated fatty acid derivatives. Therefore, fatty acid tert-butyl esters were deprotonated with strong bases, for instance lithium bis(trimethylsilyl)amide, and subsequently coupled with bromobenzene by palladium-N-heterocyclic carbene (NHC) catalysts. Furthermore, we tested the arylation activity of fatty acid tert-butyl esters towards 1,4-dibromobenzene in order to synthesize aryl-bridged diesters. These diesters were obtained in good yields of 60-80%.