Propargylierung von Carbonylverbindungen durch Umpolung von Propargylpalladiumkomplexen mit Diethylzink
Corresponding Author
Prof. Yoshinao Tamaru
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008Search for more papers by this authorSachio Goto
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorAkihiro Tanaka
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorMasamichi Shimizu
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorDr. Masanari Kimura
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorCorresponding Author
Prof. Yoshinao Tamaru
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008Search for more papers by this authorSachio Goto
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorAkihiro Tanaka
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorMasamichi Shimizu
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorDr. Masanari Kimura
Department of Applied Chemistry, Faculty of Engineering Nagasaki University, 1–14 Bunnkyo, Nagasaki 852 (Japan) Telefax: Int. + 958/47–9008
Search for more papers by this authorAbstract
References
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- 5 Alle in Tabelle 1 aufgeführten Produkte wurden durch spektroskopische Methoden (IR, 400-MHz-1H-NMR, hochauflösendes MS) und Elementaranalysen charakterisiert.
- 6 Ketone scheinen ähnlich gut zu reagieren. So ergab die Reaktion von 1 b (X = OBz) mit Acetophenon unter den in Eintrag 2 von Tabelle 1 genannten Bedingungen (THF, 29 h) 3-Methyl-2-phenyl-4-pentin-2-ol in 58% Ausbeute.
- 7 Die Komplexe III und IV mit M = ZnEt, ZnEt2− könnten über einen ähnlichen Übergangszustand gebildet worden sein, wie er für die Wanderung einer Allylgruppe von π-Allylpalladium zu Zn2 + angenommen wird [2 a].
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- 9 III mit M = ZnCl ergibt anti-2 mit hoher Selektivität: G. Zweifel, G. Hahn, J. Org. Chem. 1984, 49, 4565–4567.
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