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Synthesis 2012(3): 399-408  
DOI: 10.1055/s-0031-1289658
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes

Suren Husineca, Milos Petkovicb, Vladimir Savic*b, Milena Simicb
a Institute for Chemistry, Technology and Metallurgy (ICTM), Centre for Chemistry, P.O. Box 815, Njegoseva 12, 11000 Belgrade, Serbia
b University of Belgrade, Faculty of Pharmacy, Department of Organic Chemistry, Vojvode Stepe 450, 11221 Belgrade, Serbia
Fax: +381(11)3972 840; e-Mail: vladimir.savic@pharmacy.bg.ac.rs;
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Publication History

Received 18 October 2011
Publication Date:
29 December 2011 (online)

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Abstract

π-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.

Key words

allyl acetates - palladium catalysis - allenes - dienes - synthesis