849518-46-3Relevant academic research and scientific papers
Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon
Horino, Yoshikazu,Ishibashi, Mayo,Nakasai, Kosuke,Korenaga, Toshinobu
, (2020/08/28)
The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.
Chemoselective Luche-Type Reduction of α,β-Unsaturated Ketones by Magnesium Catalysis
Jang, Yoon Kyung,Magre, Marc,Rueping, Magnus
supporting information, p. 8349 - 8352 (2019/10/16)
The chemoselective reduction of α,β-unsaturated ketones by use of an economic and readily available Mg catalyst has been developed. Excellent yields for a wide range of ketones have been achieved under mild reaction conditions, short times, and low catalyst loadings (0.2-0.5 mol %).
Synthesis of α,β-Unsaturated Acylsilanes via Perrhenate-Catalyzed Meyer-Schuster Rearrangement of 1-Silylalkyn-3-ols
Nikolaev, Andrei,Orellana, Arturo
supporting information, p. 5796 - 5799 (2015/12/11)
We report the synthesis of α,β-unsaturated acylsilanes via the perrhenate-catalyzed Meyer-Schuster rearrangement of 1-silylalkyn-3-ols. Propargylic alcohols derived from TES-acetylene and substituted benzaldehydes can be converted to acylsilanes using a c
Oxaphospholes and bisphospholes from phosphinophosphonates and α,β-unsaturated ketones
Arkhypchuk, Anna I.,Orthaber, Andreas,Mihali, Viorica Alina,Ehlers, Andreas,Lammertsma, Koop,Ott, Sascha
supporting information, p. 13692 - 13704 (2013/10/22)
The reaction of a {W(CO)5}-stabilized phosphinophosphonate 1, (CO)5WPH(Ph)-P(O)(OEt)2, with ethynyl- (2 a-f) and diethynylketones (7-11, 18, and 19) in the presence of lithium diisopropylamide (LDA) is examined. Lithiated
Rhodium-catalyzed isomerization of α-arylpropargyl alcohols to indanones: Involvement of an unexpected reaction cascade
Shintani, Ryo,Okamoto, Kazuhiro,Hayashi, Tamio
, p. 2872 - 2873 (2007/10/03)
A rhodium-catalyzed isomerization of α-arylpropargyl alcohols to indanones has been developed under mild conditions. Considering the ease of preparation of these propargyl alcohols (terminal alkynes + aromatic aldehydes), this method provides a new way of constructing indanones with high efficiency. By the mechanistic investigations using deuterium-labeled substrates, it has also been demonstrated that the reaction goes through an unexpected cascade, with a 1,4-hydrogen shift being the turnover-limiting step of the catalytic cycle. Copyright
