116-02-9Relevant articles and documents
Haubenstock,Eliel
, p. 2368 (1962)
Coleman et al.
, p. 104 (1971)
Reduction of ketones to corresponding alcohols with magnesium metal in absolute alcohols
Kim, Ji Young,Kim, Hak Do,Seo, Min Jung,Kim, Hyoung Rae,No, Zaesung,Ha, Deok-Chan,Lee, Ge Hyeong
, p. 9 - 12 (2006)
Various aliphatic and aromatic ketones are treated with 10 equiv of magnesium metal in absolute methanol or ethanol to afford corresponding alcohols in very high yields at room temperature within 12 h.
Al-Isopropoxydiisobutylalane. a Stereoselective Reducing Agent for Reduction of cyclic Ketones to Thermodynamically More Stable Alcohols
Cha, Jin Soon,Kwon, Oh Oun
, p. 3019 - 3020 (1997)
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Cu/SiO2-catalyzed hydrogenation of cyclohexanones under very mild conditions
Ravasio, Nicoletta,Psaro, Rinaldo,Zaccheria, Federica
, p. 3943 - 3945 (2002)
Unsubstituted and alkyl-substituted cyclohexanones, including 3-oxo-steroids, can be easily hydrogenated to the corresponding alcohols at 1 atm of H2 and 60-90°C over a 8% Cu/SiO2 non-toxic, reusable catalyst with excellent selectivity.
Haubenstock
, p. 926,927 (1975)
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.
Pd/C-Al-water facilitated selective reduction of a broad variety of functional groups
Sch?fer,Ellstrom,Cho,T?r?k
, p. 1230 - 1234 (2017/03/20)
The chemoselective reduction of a broad variety of functional groups by a Pd/C-Al-H2O system is described. The reduction is based on the reaction of Al with the solvent water that in situ produces hydrogen that is utilized by the supported Pd catalyst toward the hydrogenation of the target functional groups. The hydrogenations are carried out under mild conditions and provided the products in high yields and selectivity. The reduction system appeared to be effective for a broad range of functional groups, including C-C, C-N, C-O and N-O multiple bonds, aromatic rings, hydrogenolysis of C-O, C-N and C-Halogen bonds. The appropriate selection of the reaction conditions allowed the selective preparation of different products from the same substrate. The simplicity, cost, tunability and the environmentally benign character of the catalytic system offer numerous advantages over the currently available methods.
