Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium
Publication type: Journal Article
Publication date: 2005-06-20
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Palladium/Et3B induces allyl alcohols to undergo electrophilic allylation of soft carbonucleophiles (pKa 5–14), alkyl aldehydes at the α-position, and amines, indoles, and tryptophan at the 3-position. The same catalyst, and also Pd/Et2Zn, also effect the generation of allyl anions from allyl alcohols, which react with aromatic and aliphatic aldehydes and imines to furnish homoallyl alcohols and homoallylamines, respectively, in good yields. 2-Methylenepropane-1,3-diol undergoes a sequential amphiphilic activation, generating an allyl cation and an allyl anion, and reacts with aldehydes to furnish 3-methylenecyclopentanols. The amphiphilic activation has been extended to 1,3-bis(alkoxy)-2-methylenepropanes and vinyl epoxides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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254
Total citations:
254
Citations from 2024:
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Tamaru Y. Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium // European Journal of Organic Chemistry. 2005. Vol. 2005. No. 13. pp. 2647-2656.
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Tamaru Y. Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium // European Journal of Organic Chemistry. 2005. Vol. 2005. No. 13. pp. 2647-2656.
Cite this
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TY - JOUR
DO - 10.1002/ejoc.200500076
UR - https://doi.org/10.1002/ejoc.200500076
TI - Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium
T2 - European Journal of Organic Chemistry
AU - Tamaru, Yoshinao
PY - 2005
DA - 2005/06/20
PB - Wiley
SP - 2647-2656
IS - 13
VL - 2005
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2005_Tamaru,
author = {Yoshinao Tamaru},
title = {Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium},
journal = {European Journal of Organic Chemistry},
year = {2005},
volume = {2005},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/ejoc.200500076},
number = {13},
pages = {2647--2656},
doi = {10.1002/ejoc.200500076}
}
Cite this
MLA
Copy
Tamaru, Yoshinao. “Activation of Allyl Alcohols as Allyl Cations, Allyl Anions, and Amphiphilic Allylic Species by Palladium.” European Journal of Organic Chemistry, vol. 2005, no. 13, Jun. 2005, pp. 2647-2656. https://doi.org/10.1002/ejoc.200500076.