Reactive organoallyl species generated from aryl halides and allene: allylation of alpha,beta-unsaturated aldehydes and cyclic ketones employing Pd/In transmetallation processes
Apstrakt
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.
Izvor:
Tetrahedron Letters, 2008, 64, 37, 8731-8737Izdavač:
- Pergamon-Elsevier Science Ltd, Oxford
Finansiranje / projekti:
- Leeds University
DOI: 10.1016/j.tet.2008.06.100
ISSN: 0040-4020
WoS: 000258841100020
Scopus: 2-s2.0-48149113762
Institucija/grupa
PharmacyTY - 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 . .