α-Arylation of saturated fatty acids

Authors


Correspondence: Prof. Michael A. R. Meier, Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg-6, Building 30.42, 76131 Karlsruhe, Germany

E-mail: m.a.r.meier@kit.edu

Abstract

In this study, we take advantage of the α-CH-acidity of fatty acid esters in order to obtain α-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%.

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