56705-38-5Relevant articles and documents
The Stereochemistry of Condensation Reactions of (+/-)-3-Phenylbutan-2-one with Phenylmetallic Compounds as a Function of the Reagent Nucleophilicity
Arjona, Odon,Perez-Ossorio, Rafael,Perez-Rubalcaba, Alfredo,Quiroga, Maria L.
, p. 452 - 453 (1982)
The influence of changing the metall and adding electrophilic catalysts or iron(III) and copper(I) salts on the stereochemical path of the nucleophilic addition of organometallics to (+/-)-3-phenylbutan-2-one is discussed.
Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins
Bachmann, Stephan,Bigler, Raphael,Denmark, Scott E.,Gosselin, Francis,Han, Chong,Hildbrand, Stefan,Mack, Kyle A.,Pfaltz, Andreas,Scalone, Michelangelo,Shen, Jeff,Tosatti, Paolo,Zhang, Haiming
supporting information, p. 2844 - 2849 (2020/02/05)
Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio- and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is demonstrated by the successful hydrogenation of a wide variety of electronically and sterically diverse olefins in excellent yield and high enantio- and diastereoselectivity.
Bimetallic Nanoparticles in Supported Ionic Liquid Phases as Multifunctional Catalysts for the Selective Hydrodeoxygenation of Aromatic Substrates
Offner-Marko, Lisa,Bordet, Alexis,Moos, Gilles,Tricard, Simon,Rengshausen, Simon,Chaudret, Bruno,Luska, Kylie L.,Leitner, Walter
supporting information, p. 12721 - 12726 (2018/09/12)
Bimetallic iron–ruthenium nanoparticles embedded in an acidic supported ionic liquid phase (FeRu@SILP+IL-SO3H) act as multifunctional catalysts for the selective hydrodeoxygenation of carbonyl groups in aromatic substrates. The catalyst material is assembled systematically from molecular components to combine the acid and metal sites that allow hydrogenolysis of the C=O bonds without hydrogenation of the aromatic ring. The resulting materials possess high activity and stability for the catalytic hydrodeoxygenation of C=O groups to CH2 units in a variety of substituted aromatic ketones and, hence, provide an effective and benign alternative to traditional Clemmensen and Wolff–Kishner reductions, which require stoichiometric reagents. The molecular design of the FeRu@SILP+IL-SO3H materials opens a general approach to multifunctional catalytic systems (MM′@SILP+IL-func).
Semiconductor Phostocatalysis. ZnS-Nanocrystallite-Catalyzed Photooxidation of Organic Compounds
Yanagida, Shozo,Kawakami, Hiroshi,Midori, Yoshihide,Kizumoto, Hirotoshi,Pac, Chongjin,Wada, Yuji
, p. 1811 - 1824 (2007/10/03)
Freshly prepared ZnS (nano-ZnS) suspensions catalyze photooxidation of organic substrates under band-gap irradiation with water as a good electron acceptor, while H2 evolves concomitantly.The organic substrates with hetero atoms or carbon-carbon double bonds (?-bonds), such as triethylamine (TEA), diethylamine (DEA), methanol, ethanol, cyclopentene, cyclohexene, 2-methylfuran, toluene, and ethylbenzene, undergo effective one-hole oxidation.This leads to efficient carbon-carbon bond forming reactions between cumulatively formed radicals at the α-carbon adjacent to the hetero atom or the ?-bond.The photooxidation in the presence of a larger quantity of water results in successive oxidation of the intermediary α-carbon radicals, giving the two-hole oxidation products, e.g., DEA and acetaldehyde from TEA and formaldehyde from methanol.The formation of the intermediary α-carbon radical has been clarified by ESR analysis using 2-propanol as an organic substrate.Semi-empirical molecular orbital calculations suggest that the nano-ZnS-catalyzed photooxidation should be predictable from energetics in the formation of the α-carbon radicals through one-hole oxidation and deprotonation, and from change in the bond order of αC-H bond of the α-carbon cation radicals.
