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Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes

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2008
1120.pdf (960.7Kb)
Authors
Cleghorn, Laura A. T.
Grigg, Ronald
Savić, Vladimir
Simić, Milena
Article (Published version)
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Abstract
Allylation of alpha,beta-unsaturated aldehydes and cyclic ketones promoted by Pd/In transmetallation processes has been Studied. The unsaturated aldehydes underwent regioselective 1,2-addition to afford secondary homoally alcohols. The reactions have been performed using Pd(OAc)(2)/PPh(3) as catalytic system and metallic indium affording the products in good yields. The same transformation with unsaturated ketones proved to be less efficient, while saturated cyclic ketones delivered generally excellent yields in the presence of Cul. In these latter processes the presence of a distal heteroatom influences the reaction rate.
Source:
Tetrahedron Letters, 2008, 64, 37, 8731-8737
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
  • Leeds University

DOI: 10.1016/j.tet.2008.06.100

ISSN: 0040-4020

WoS: 000258841100020

Scopus: 2-s2.0-48149113762
[ Google Scholar ]
10
9
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/1122
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Cleghorn, Laura A. T.
AU  - Grigg, Ronald
AU  - Savić, Vladimir
AU  - Simić, Milena
PY  - 2008
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1122
AB  - Allylation of alpha,beta-unsaturated aldehydes and cyclic ketones promoted by Pd/In transmetallation processes has been Studied. The unsaturated aldehydes underwent regioselective 1,2-addition to afford secondary homoally alcohols. The reactions have been performed using Pd(OAc)(2)/PPh(3) as catalytic system and metallic indium affording the products in good yields. The same transformation with unsaturated ketones proved to be less efficient, while saturated cyclic ketones delivered generally excellent yields in the presence of Cul. In these latter processes the presence of a distal heteroatom influences the reaction rate.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron Letters
T1  - Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes
VL  - 64
IS  - 37
SP  - 8731
EP  - 8737
DO  - 10.1016/j.tet.2008.06.100
ER  - 
@article{
author = "Cleghorn, Laura A. T. and Grigg, Ronald and Savić, Vladimir and Simić, Milena",
year = "2008",
abstract = "Allylation of alpha,beta-unsaturated aldehydes and cyclic ketones promoted by Pd/In transmetallation processes has been Studied. The unsaturated aldehydes underwent regioselective 1,2-addition to afford secondary homoally alcohols. The reactions have been performed using Pd(OAc)(2)/PPh(3) as catalytic system and metallic indium affording the products in good yields. The same transformation with unsaturated ketones proved to be less efficient, while saturated cyclic ketones delivered generally excellent yields in the presence of Cul. In these latter processes the presence of a distal heteroatom influences the reaction rate.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron Letters",
title = "Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes",
volume = "64",
number = "37",
pages = "8731-8737",
doi = "10.1016/j.tet.2008.06.100"
}
Cleghorn, L. A. T., Grigg, R., Savić, V.,& Simić, M.. (2008). Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes. in Tetrahedron Letters
Pergamon-Elsevier Science Ltd, Oxford., 64(37), 8731-8737.
https://doi.org/10.1016/j.tet.2008.06.100
Cleghorn LAT, Grigg R, Savić V, Simić M. Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes. in Tetrahedron Letters. 2008;64(37):8731-8737.
doi:10.1016/j.tet.2008.06.100 .
Cleghorn, Laura A. T., Grigg, Ronald, Savić, Vladimir, Simić, Milena, "Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes" in Tetrahedron Letters, 64, no. 37 (2008):8731-8737,
https://doi.org/10.1016/j.tet.2008.06.100 . .

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