2550-26-7Relevant articles and documents
Hydrogenation of α,β-Unsaturated Carbonyl Compounds by Carbon monoxide and Water with Rh6(CO)16 Catalyst under Mild Conditions
Joh, Takashi,Fujiwara, Keisuke,Takahashi, Shigetoshi
, p. 978 - 980 (1993)
By controlling such factors as the concentration of water and amine, the carbon-carbon double bond of α,β-unsaturated carbonyl compounds could be selectively hydrogenated under mild water-gas shift reaction (WGSR) conditions using a Rh6(CO)16-Et3N catalys
Diastereoselective dl-Hydrocoupling of Benzalacetones by Electroreduction
Kise, Naoki,Kitagishi, Yasuo,Ueda, Nasuo
, p. 959 - 963 (2004)
Electroreduction of benzalacetones with an undivided cell in Et 4NOTs/acetonitrile gave cyclized dl-hydrodimers as mixtures of two diastereomers. The hydrodimerization proceeded stereoselectively to afford linear dl-hydrodimers, and the following cyclization led to two thermodynamically stable diasteromers of cyclopentanols.
De Puy,Breitbeil
, p. 2176 (1963)
Enzyme-catalysed enantioselective oxidation of alcohols by air exploiting fast electrochemical nicotinamide cycling in electrode nanopores
Wan, Lei,Heath, Rachel S.,Siritanaratkul, Bhavin,Megarity, Clare F.,Sills, Adam J.,Thompson, Matthew P.,Turner, Nicholas J.,Armstrong, Fraser A.
, p. 4958 - 4963 (2019)
Enantioselective conversion of alcohols to ketones using air as the oxidant is achieved with high rates and efficiency using an indium tin oxide (ITO) electrode in which an alcohol dehydrogenase and a photosynthetic NADPH recycling enzyme are confined within nanopores. The massive catalytic enhancement arising from nanoconfinement is exploited in an air-driven electrochemical cell, which requires no complicating control features yet allows continuous monitoring of the reaction via the current that flows between anode (ITO: Organic chemistry) and cathode (Pt: O2 from air).
TRANSFER HYDROGENATION BETWEEN ALCOHOLS AND α,β UNSATURATED KETONES WITH RhH(PPh3)3 AS CATALYST. EVIDENCE FOR REGIOSPECIFICITY AND AN UNUSUAL RATE-LIMITING STEP
Beaupere, D.,Bauer, P.,Nadjo, L.,Uzan, R.
, p. C12 - C14 (1982)
In the hydrogen transfer between an alcohol and an α,β-unsaturated ketone with RhH(PPh3)4 as catalyst under mild conditions the breaking of the O-H bond is, unusually, the rate-determining step, and the hydroxylic hydrogen is selectively transferred to the α-carbon of the ketone.
Homo-coupling reactions of alkenyl- and arylfluorosilanes mediated by a copper(I) salt
Nishihara, Yasushi,Ikegashira, Kazutaka,Toriyama, Fumihiko,Mori, Atsunori,Hiyama, Tamejiro
, p. 985 - 990 (2000)
Homo-coupling reactions of an alkenyl- or arylsilane readily occur with a copper(I) salt in an aprotic polar solvent such as N, N-dimethylformamide or dimethyl sulfoxide under an aerobic condition to give the corresponding conjugated dienes or biaryls, respectively. Optimization of a copper salt and a solvent for the homo-coupling reaction is discussed. The formation of the organocopper intermediates is evidenced by trapping experiments with iodine and by a conjugate addition to methyl vinyl ketone.
RADICAL REACTION OF ACETONYLTRIBUTYLSTANNANE WITH α-(PHENYLSELENO)CARBONYL COMPOUNDS: A NOVEL PROCEDURE FOR PREPARATION OF 1,4-DICARBONYL COMPOUNDS
Watanabe, Yoshihiko,Yoneda, Tetsuo,Ueno, Yoshio,Toru, Takeshi
, p. 6669 - 6672 (1990)
Radical reaction of acetonyltributylstannane 1 with α-(phenylseleno)carbonyl compounds 2 gave 1,4-dicarbonyl compounds in high yield.The SH2' mechanism via the stannyl enolate in equilibrium with acetonylstannane is postulated.
Stereo-Divergent Enzyme Cascades to Convert Racemic 4-Phenyl-2-Butanol into either (S)- or (R)-Corresponding Chiral Amine
Paradisi, Francesca,Romero-Fernandez, Maria
, (2022/03/08)
The synthesis of enantiopure chiral amines from racemic alcohols is a key transformation in the chemical industry, e. g., in the production of active pharmaceutical ingredients (APIs). However, this reaction remains challenging. In this work, we propose a one-pot enzymatic cascade for the direct conversion of a racemic alcohol into either (S)- or (R)-enantiomers of the corresponding amine, with in-situ cofactor recycling. This enzymatic cascade consists of two enantio-complementary alcohol dehydrogenases, both NADH and NADPH oxidase for in-situ recycling of NAD(P)+ cofactors, and either (S)- or (R)-enantioselective transaminase. This cell-free biocatalytic system has been successfully applied to the conversion of racemic 4-phenyl-2-butanol into the high value (S)- or (R)-enantiomers of the amine reaching good (73 % (S)) and excellent (>99 % (R)) enantioselectivities.
Selective upgrading of biomass-derived benzylic ketones by (formic acid)–Pd/HPC–NH2 system with high efficiency under ambient conditions
Chen, Yuzhuo,Chen, Zhirong,Gong, Yutong,Mao, Shanjun,Ning, Honghui,Wang, Yong,Wang, Zhenzhen
, p. 3069 - 3084 (2021/11/16)
Upgrading biomass-derived phenolic compounds provides a valuable approach for the production of higher-value-added fuels and chemicals. However, most established catalytic systems display low hydrodeoxygenation (HDO) activities even under harsh reaction conditions. Here, we found that Pd supported on –NH2-modified hierarchically porous carbon (Pd/HPC–NH2) with formic acid (FA) as hydrogen source exhibits unprecedented performance for the selective HDO of benzylic ketones from crude lignin-derived oxygenates. Designed experiments and theoretical calculations reveal that the H+/H? species generated from FA decomposition accelerates nucleophilic attack on carbonyl carbon in benzylic ketones and the formate species formed via the esterification of intermediate alcohol with FA expedites the cleavage of C–O bonds, achieving a TOF of 152.5 h?1 at 30°C for vanillin upgrading, 15 times higher than that in traditional HDO processes (~10 h?1, 100°C–300°C). This work provides an intriguing green route to produce transportation fuels or valuable chemicals from only biomass under mild conditions.