α‐Arylation of saturated fatty acids

Abstract

In this study, we take advantage of the a-CH-acidity of fatty acid esters in order to obtain a-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-Nheterocyclic carbene (NHC) catalysts. Furthermore, we tested the arylation activity of fatty acid tertbutyl esters towards 1,4-dibromobenzene in order to synthesize aryl-bridged diesters. These diesters were obtained in good yields of 60-80%.

Structure–properties relationship of fatty acid-based thermoplastics as synthetic polymer mimics

“…have synthesized thermoplastic polyamides from α-arylated fatty acid derivatives which were synthesized taking advantage of the α-CH-acidity of fatty acid esters. 175 The authors have performed the palladium catalyzed α-arylation reaction between 1,4-dibromobenzene and fatty acid tert-butyl esters in good yields (60-80%). After cleavage of the ester functions in acidic conditions to free carboxylic acids, the latter were polymerized with 1,6-hexanediamine but only low molecular weight oligomers (Mn = 5.1 kg mol −1 ) were obtained.…”