Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes
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pi-Allylpalladium intermediates are known to participate efficiently in transformations involving nucleophilic species. Exploring these processes, we have developed a method for the preparation of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes. Reactions of aryl iodides with either of these two classes of compounds and excess sodium acetate in the presence of Pd(OAc) (2) and Ph3P as the catalytic system afforded the respective allyl acetates in moderate to good yields. The scope of this process has been investigated. The described method is an addition to the synthetic repertoire for the preparation of allyl acetates, and may be useful, in particular, for the synthesis of structurally complex compounds of this type.
Keywords:allyl acetates / palladium catalysis / allenes / dienes / synthesis
Source:Synthesis, 2012, 44, 3, 399-408
- Stuttgart : Georg Thieme Verlag Kg