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.
TY - JOUR
AU - Husinec, Suren
AU - Jadranin, Milka
AU - Marković, Rade
AU - Petković, Miloš
AU - Savić, Vladimir
AU - Todorović, Nina
PY - 2010
UR - http://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",
url = "http://farfar.pharmacy.bg.ac.rs/handle/123456789/1382",
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.
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. Tetrahedron-Asymmetry. 2010;51(31):4066-4068
