Palladium-catalysed synthesis of allyl acetates from allenes
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2010
Authors
Husinec, SurenJadranin, Milka
Marković, Rade
Petković, Miloš
Savić, Vladimir
Todorović, Nina
Article (Published version)
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Allyl acetates were synthesised from allenes utilising methodology based on the general reactivity of pi-allyl palladium intermediates which participate efficiently in transformations involving nucleophiles. Reactions of allenes and aryl iodides in the presence of AcONa and Pd(OAc)(2)/PPh(3) as the catalytic system afforded allyl acetates in moderate to good yields. Monosubstituted allenes, depending on their structure, produced either a separable mixture of two regioisomeric products or a single regioisomer. As allylic acetates can be easily hydrolysed, the methodology is applicable for the synthesis of allyl alcohols as well.
Source:
Tetrahedron-Asymmetry, 2010, 51, 31, 4066-4068Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Sinteza, kvantitativni odnosi između strukture/osobina i aktivnosti, fizičko-hemijska karakterizacija i analiza farmakološki aktivnih supstanci (RS-MESTD-MPN2006-2010-142071)
DOI: 10.1016/j.tetlet.2010.05.136
ISSN: 0040-4039
WoS: 000280053600018
Scopus: 2-s2.0-77954031310
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PharmacyTY - JOUR AU - Husinec, Suren AU - Jadranin, Milka AU - Marković, Rade AU - Petković, Miloš AU - Savić, Vladimir AU - Todorović, Nina PY - 2010 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1382 AB - Allyl acetates were synthesised from allenes utilising methodology based on the general reactivity of pi-allyl palladium intermediates which participate efficiently in transformations involving nucleophiles. Reactions of allenes and aryl iodides in the presence of AcONa and Pd(OAc)(2)/PPh(3) as the catalytic system afforded allyl acetates in moderate to good yields. Monosubstituted allenes, depending on their structure, produced either a separable mixture of two regioisomeric products or a single regioisomer. As allylic acetates can be easily hydrolysed, the methodology is applicable for the synthesis of allyl alcohols as well. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron-Asymmetry T1 - Palladium-catalysed synthesis of allyl acetates from allenes VL - 51 IS - 31 SP - 4066 EP - 4068 DO - 10.1016/j.tetlet.2010.05.136 ER -
@article{ author = "Husinec, Suren and Jadranin, Milka and Marković, Rade and Petković, Miloš and Savić, Vladimir and Todorović, Nina", year = "2010", abstract = "Allyl acetates were synthesised from allenes utilising methodology based on the general reactivity of pi-allyl palladium intermediates which participate efficiently in transformations involving nucleophiles. Reactions of allenes and aryl iodides in the presence of AcONa and Pd(OAc)(2)/PPh(3) as the catalytic system afforded allyl acetates in moderate to good yields. Monosubstituted allenes, depending on their structure, produced either a separable mixture of two regioisomeric products or a single regioisomer. As allylic acetates can be easily hydrolysed, the methodology is applicable for the synthesis of allyl alcohols as well.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron-Asymmetry", title = "Palladium-catalysed synthesis of allyl acetates from allenes", volume = "51", number = "31", pages = "4066-4068", doi = "10.1016/j.tetlet.2010.05.136" }
Husinec, S., Jadranin, M., Marković, R., Petković, M., Savić, V.,& Todorović, N.. (2010). Palladium-catalysed synthesis of allyl acetates from allenes. in Tetrahedron-Asymmetry Pergamon-Elsevier Science Ltd, Oxford., 51(31), 4066-4068. https://doi.org/10.1016/j.tetlet.2010.05.136
Husinec S, Jadranin M, Marković R, Petković M, Savić V, Todorović N. Palladium-catalysed synthesis of allyl acetates from allenes. in Tetrahedron-Asymmetry. 2010;51(31):4066-4068. doi:10.1016/j.tetlet.2010.05.136 .
Husinec, Suren, Jadranin, Milka, Marković, Rade, Petković, Miloš, Savić, Vladimir, Todorović, Nina, "Palladium-catalysed synthesis of allyl acetates from allenes" in Tetrahedron-Asymmetry, 51, no. 31 (2010):4066-4068, https://doi.org/10.1016/j.tetlet.2010.05.136 . .