16201-66-4Relevant academic research and scientific papers
Trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives
Bergander, Klaus,Glorius, Frank,Heusler, Arne,Wollenburg, Marco
, p. 11365 - 11370 (2020/11/24)
A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.
Cobalt-Nanoparticles Catalyzed Efficient and Selective Hydrogenation of Aromatic Hydrocarbons
Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Alshammari, Ahmad S.,Altamimi, Rashid M.,Kreyenschulte, Carsten,Pohl, Marga-Martina,Lund, Henrik,Jagadeesh, Rajenahally V.,Beller, Matthias
, p. 8581 - 8591 (2019/09/12)
The development of inexpensive and practical catalysts for arene hydrogenations is key for future valorizations of this general feedstock. Here, we report the development of cobalt nanoparticles supported on silica as selective and general catalysts for such reactions. The specific nanoparticles were prepared by assembling cobalt-pyromellitic acid-piperazine coordination polymer on commercial silica and subsequent pyrolysis. Applying the optimal nanocatalyst, industrial bulk, substituted, and functionalized arenes as well as polycyclic aromatic hydrocarbons are selectively hydrogenated to obtain cyclohexane-based compounds under industrially viable and scalable conditions. The applicability of this hydrogenation methodology is presented for the storage of H2 in liquid organic hydrogen carriers.
Raney Ni-Al alloy-mediated reduction of alkylated phenols in water
Tan, Song-Liang,Liu, Guo-Bin,Gao, Xiang,Thiemann, Thies
experimental part, p. 5 - 7 (2009/09/06)
Raney Ni-Al alloy in a dilute aqueous alkaline solution has been shown to be a very powerful reducing agent in the hydrogenation of phenol and alkylated phenols to the corresponding cyclohexanol derivatives.
Stereoselective hydrogenation of tert-butylphenols over charcoal-supported rhodium catalyst in supercritical carbon dioxide solvent
Hiyoshi, Norihito,Rode, Chandrashekhar V.,Sato, Osamu,Tetsuka, Hiroyuki,Shirai, Masayuki
, p. 57 - 68 (2008/09/17)
Hydrogenation of 2-, 3-, and 4-tert-butylphenols was studied over a charcoal-supported rhodium catalyst in supercritical carbon dioxide (scCO2) solvent, and the results were compared with those in organic solvents. In the hydrogenation of 4-ter
Highly regio- and stereoselective reductions of carbonyl compounds in aqueous glycosidic media
Denis, Cecile,Laignel, Benoit,Plusquellec, Daniel,Le Marouille, Jean-Yves,Botrel, Alain
, p. 53 - 56 (2007/10/02)
Highly regioselective reductions of α,β-unsaturated ketones to the corresponding allylic alcohols were performed in essentially quantitative yields in aqueous media containing either glycosidic surfactants or amphiphilic carbohydrates. Reductions of cyclohexanones and cyclohexenones lead under the same conditions, stereoselectively to reduced compounds bearing an equatorial alcohol function. Hydrophobic interactions between amphiphilic carbohydrates and lipophilic substrates were modelized and should account for the observed stereodifferentiation.
The functionalization of saturated hydrocarbons. Part 24. The use of tert-butyl hydroperoxide: GoAggIV and GoAggV
Barton, Derek H. R.,Chavasiri, Warinthorn
, p. 19 - 30 (2007/10/02)
The use of tert-butyl hydroperoxide as an oxidant in Gif-type systems (GoAggIV and GoAgfV) catalyzed by various Fe(III) species is examined. Regioselectivity studids of these systems have revealed several characteristics similar to those observed for other prdviously reported Gif-type reactions. A common rdaction pathway for the GoAggIV and GoAggV oxidation systems and other Gif-type reactions (from alkane via alkyl hydroperoxide to ketone or alcohol) is seen.
The Use of Bismuth(III) Acetate in 'Wet' and 'Dry' Prevost Reactions
Trainor, Robert W.,Deacon, Glen B.,Jackson, W. Roy,Giunta, Nunzio
, p. 1265 - 1280 (2007/10/02)
cis-Diol and trans-diol derivatives can be prepared from alkenes by reaction with iodine and bismuth(III) acetate in 'wet' and 'dry' acetic acid, respectively.Reactions using lesser amounts of bismuth(III) acetate under 'dry' conditions give iodo acetates and under 'wet' conditions a mixture of iodohydrins and iodo ethers.Comparison of these reactions with those promoted by silver, copper, mercury and thallium salts is included.
γ-Silicon Stabilization of Carbonium Ions in Solvolysis. 4. Solvolysis of cis- and trans-3-(Trimethylsilyl)cyclohexyl and -3-tert-Butylcyclohexyl p-Bromobenzenesulfonates
Shiner, V.J.,Ensinger, Mark W.,Kriz, George S.,Halley, Karen A.
, p. 653 - 661 (2007/10/02)
The solvolyses of cis- and trans-3-(trimethylsilyl)cyclohexyl and -3-tert-butylcyclohexyl p-bromobenzenesulfonates (1-4) have been examined in several ethanol- and trifluoroethanol-water solvent mixtures.The α- and β-deuterium kinetic isotope effects have
Stereochemical Aspects of Oxirane Ring Opening. Heterogeneous Catalytic Deuterolysis of cis and trans-1,2-Epoxy-4-t-butylcyclohexanes
Ishiyama, Jun-ichi,Yashima, Hiroaki,Matsuo, Hironobu,Senda, Yasuhisa,Imaizumi, Shin,et al.
, p. 989 - 992 (2007/10/02)
2H NMR analysis of deuterolyzed products from cis- and trans-1,2-epoxy-4-t-butylcyclohexane indicated that the cleavage of the oxirane C-O bond proceeds with inversion of configuration over noble metal catalysts except for Ru, while with retention over Co
