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.
Cobalt-catalyzed Divergent Markovnikov and Anti-Markovnikov Hydroamination
Zhang, Xiang-Gui,He, Zi-Xin,Guo, Peng,Chen, Zheng,Ye, Ke-Yin
supporting information, p. 22 - 26 (2022/01/04)
Catalytic hydroamination of the readily available alkenes is among the most straightforward means to construct diverse alkyl amines. To this end, the facile access to both regioselectivity, i.e., Markovnikov or anti-Markovnikov hydroamination, with minimum reaction-parameter alternation, remains challenging. Herein, we report a cobalt-catalyzed highly selective and divergent Markovnikov and anti-Markovnikov hydroamination of alkenes, in which the switch of regioselectivity is achieved simply by the variation of the addition sequence of 9-BBN.
Deep eutectic solvents as H2-sources for Ru(II)-catalyzed transfer hydrogenation of carbonyl compounds under mild conditions
Cavallo, Marzia,Arnodo, Davide,Mannu, Alberto,Blangetti, Marco,Prandi, Cristina,Baratta, Walter,Baldino, Salvatore
supporting information, (2021/02/22)
The employment of easily affordable ruthenium(II)-complexes as pre-catalysts in the transfer hydrogenation of carbonyl compounds in deep eutectic media is described for the first time. The eutectic mixture tetrabutylammonium bromide/formic acid = 1/1 (TBABr/HCOOH = 1/1) acts both as reaction medium and hydrogen source. The addition of a base is required for the process to occur. An extensive optimization of the reaction conditions has been carried out, in terms of catalyst loading, type of complexes, H2-donors, reaction temperature and time. The combination of the dimeric complex [RuCl(p-cymene)-μ-Cl]2 (0.01–0.05 eq.) and the ligand dppf (1,1′-ferrocenediyl-bis(diphenylphosphine)ferrocene) in 1/1 molar ratio has proven to be a suitable catalytic system for the reduction of several and diverse aldehydes and ketones to their corresponding alcohols under mild conditions (40–60 °C) in air, showing from moderate to excellent tolerability towards different functional groups (halogen, cyano, nitro, phenol). The reduction of imine compounds to their corresponding amine derivatives was also studied. In addition, the comparison between the results obtained in TBABr/HCOOH and in organic solvents suggests a non-innocent effect of the DES medium during the process.
