Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes
Abstract
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 / synthesisSource:
Synthesis, 2012, 44, 3, 399-408Publisher:
- Stuttgart : Georg Thieme Verlag Kg
Funding / projects:
DOI: 10.1055/s-0031-1289658
ISSN: 0039-7881
WoS: 000300255100013
Scopus: 2-s2.0-84856231784
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IHTMTY - JOUR AU - Husinec, Suren AU - Petković, Miloš AU - Savić, Vladimir AU - Simić, Milena PY - 2012 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4173 AB - 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. PB - Stuttgart : Georg Thieme Verlag Kg T2 - Synthesis T1 - Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes VL - 44 IS - 3 SP - 399 EP - 408 DO - 10.1055/s-0031-1289658 ER -
@article{ author = "Husinec, Suren and Petković, Miloš and Savić, Vladimir and Simić, Milena", year = "2012", abstract = "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.", publisher = "Stuttgart : Georg Thieme Verlag Kg", journal = "Synthesis", title = "Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes", volume = "44", number = "3", pages = "399-408", doi = "10.1055/s-0031-1289658" }
Husinec, S., Petković, M., Savić, V.,& Simić, M.. (2012). Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes. in Synthesis Stuttgart : Georg Thieme Verlag Kg., 44(3), 399-408. https://doi.org/10.1055/s-0031-1289658
Husinec S, Petković M, Savić V, Simić M. Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes. in Synthesis. 2012;44(3):399-408. doi:10.1055/s-0031-1289658 .
Husinec, Suren, Petković, Miloš, Savić, Vladimir, Simić, Milena, "Synthesis of Allyl Acetates via Palladium-Catalysed Functionalisation of Allenes and 1,3-Dienes" in Synthesis, 44, no. 3 (2012):399-408, https://doi.org/10.1055/s-0031-1289658 . .