Abstract
A versatile approach to the synthesis of new cardanol derivatives through a combination of aromatic iodination of 3-n -pentadecylphenol and palladium-catalysed cross-coupling reactions has been developed. The extent of aromatic iodination is controlled by stoichiometry and affords either the mono-, di- or tri-iodo-cardanol derivatives. Suzuki, Heck and Sonogashira protocols were successfully applied for the vinylation, arylation and alkynylation of the iodo-cardanols. 2,4-Diiodo-5-n -pentadecylphenol underwent an unusual sequential regioselective dehalogenation/vinylation reaction. Sequential alkynylation/cyclisation of 2-iodo-3-n -pentadecylphenol derivatives were also investigated.
Key words
aromatic substitution - halogenation - palladium - Heck reaction - cross-coupling
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