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α‐ A rylation of saturated fatty acids
Author(s) -
Kolb Nicolai,
Hofsäß Robert,
Meier Michael A. R.
Publication year - 2013
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201300082
Subject(s) - chemistry , fatty acid , organic chemistry , bromobenzene , trimethylsilyl , aryl , catalysis , lithium amide , amide , deprotonation , lithium (medication) , enantioselective synthesis , medicine , endocrinology , ion , alkyl
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%.