Palladium-Tetraphosphine Catalysed Heck Reaction with Simple Alkenes: Influence of Reaction Conditions on the Migration of the Double Bond

 

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Abstract

The Heck reaction of aryl halides with simple alk-1-enes is a powerful method for the synthesis of (E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon double bond along the alkyl chain. We observed that this migration could be partially controlled using appropriate reaction conditions. The ramification of the alkyl chain and the substituents on the aryl halide has also an important influence on this migration. The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[Pd(C₃H₅)Cl]₂ system catalyses efficiently the Heck reaction of a wide variety of aryl halides with the linear alkenes oct-1-ene and dec-1-ene or the branched alkenes 4-methylhex-1-ene, 5-methylhex-1-ene, allylcyclopentane, or allylcyclohexane. In most cases, selectivities of 70-80% were obtained. In some cases, up to 97% in favour of (E)-1-arylalk-1-enes can be observed. Moreover several reactions can be performed using very low catalyst loadings.

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