5402-28-8Relevant articles and documents
Heterogeneous Hydroxyl-Directed Hydrogenation: Control of Diastereoselectivity through Bimetallic Surface Composition
Shumski, Alexander J.,Swann, William A.,Escorcia, Nicole J.,Li, Christina W.
, p. 6128 - 6134 (2021/05/29)
Directed hydrogenation, in which product selectivity is dictated by the binding of an ancillary directing group on the substrate to the catalyst, is typically catalyzed by homogeneous Rh and Ir complexes. No heterogeneous catalyst has been able to achieve equivalently high directivity due to a lack of control over substrate binding orientation at the catalyst surface. In this work, we demonstrate that Pd-Cu bimetallic nanoparticles with both Pd and Cu atoms distributed across the surface are capable of high conversion and diastereoselectivity in the hydroxyl-directed hydrogenation reaction of terpinen-4-ol. We postulate that the OH directing group adsorbs to the more oxophilic Cu atom while the olefin and hydrogen bind to adjacent Pd atoms, thus enabling selective delivery of hydrogen to the olefin from the same face as the directing group with a 16:1 diastereomeric ratio.
Restricted rotation due to the lack of free space within a capsule translates into product selectivity: Photochemistry of cyclohexyl phenyl ketones within a water-soluble organic capsule
Kulasekharan, Revathy,Choudhury, Rajib,Prabhakar, Rajeev,Ramamurthy
supporting information; experimental part, p. 2841 - 2843 (2011/05/05)
The rotational mobility of organic guest molecules when included within a confined capsule is restricted and this feature could be translated into product selectivity as established with the photochemical behavior of cyclohexyl phenyl ketones. The Royal Society of Chemistry.
Functionalization of Saturated Hydrocarbons. Part 4. The Gif System for Selective Oxidation using Molecular Oxygen
Barton, Derek H. R.,Boivin, Jean,Gastiger, Michel,Morzycki, Jacek,Hay-Motherwell, Robyn S.,et al.
, p. 947 - 956 (2007/10/02)
Various systems for the selective oxidation of saturated hydrocarbons have been developed.These are based on the idea of an iron catalyst which is reduced by electron transfer and oxidized by molecular oxygen simultaneously in the presence of a source of protons.Four modifications of this system (the Gif system) have been devised of which the best (Gif IV) consists of an iron catalyst with metallic zinc as the reductant, acetic acid as the proton source and pyridine as the solvent.At room temperature, using oxygen or air, saturated hydrocarbons are oxidized selectively to ketones in isolated yields superior to those reported for comparable model systems.