112-43-6Relevant articles and documents
N-heterocyclic carbene piano-stool iron complexes as efficient catalysts for hydrosilylation of carbonyl derivatives
Jiang, Fan,Bezier, David,Sortais, Jean-Baptiste,Darcel, Christophe
, p. 239 - 244 (2011)
Hydrosilylation with well defined piano-stool iron(II) complexes bearing both N-heterocyclic carbene and cyclopentadienyl ligands was accomplished with both aldehydes and ketones. Typically, the reduction of aldehydes exhibited good activities (full reduction at 30a°C in 3ah), whereas for ketones, the reaction need 16ah at 70a°C to obtain good conversions. Of notable interest is the use of visible light irradiation to generate one of the active catalyst.
Harnessing open-source technology for low-cost automation in synthesis: Flow chemical deprotection of silyl ethers using a homemade autosampling system
O'Brien, Matthew,Konings, Lisette,Martin, Matthew,Heap, Jordan
, p. 2409 - 2413 (2017)
An inexpensive homemade 3-axis autosampler was used to facilitate the automation of an acid catalysed flow chemical desilylation reaction. Harnessing open-source software technologies (Python, OpenCV), an automated computer-vision controlled liquid-liquid extraction step was used to provide effective inline purification. A Raspberry Pi single-board computer was employed to interface with the motors used in the autosampler and actuated fluidic valves.
Photochemical deprotection of nitro-substituted benzenesulfenates via photoinduced electron transfer
Wakamatsu, Kan,Kouda, Mitsuru,Shimaoka, Kazuyoshi,Yamada, Haruo
, p. 6395 - 6398 (2004)
The photochemical deprotection of alkyl 2,4-dinitrobenzenesulfenate or alkyl 2-nitrobenzenesulfenate was successfully achieved by addition of triethylamine, while it was unsuccessful without triethylamine. The sulfur-oxygen bond cleavage is thought to occ
Evaluating a sodium dispersion reagent for the Bouveault-Blanc reduction of esters
An, Jie,Work, D. Neil,Kenyon, Craig,Procter, David J.
, p. 6743 - 6747 (2014)
A new sodium dispersion reagent has been evaluated for the reduction of esters. Na-D15, a sodium dispersion with sodium particle size of 5-15 μm, is a nonpyrophoric reagent that can be handled in air. In this study, a broad range of aliphatic ester substrates were reduced to primary alcohols by Na-D15/i-PrOH with good yields. The method compares favorably with modern metal hydride reductions and is much safer and efficient than the traditional Bouveault-Blanc reduction.
Hydrosilylation of aldehydes and ketones catalyzed by half-sandwich manganese(I) N-heterocyclic carbene complexes
Zheng, Jianxia,Elangovan, Saravanakumar,Valyaev, Dmitry A.,Brousses, Remy,Cesar, Vincent,Sortais, Jean-Baptiste,Darcel, Christophe,Lugan, Noel,Lavigne, Guy
, p. 1093 - 1097 (2014)
Easily available manganese(I) N-heterocyclic carbene (NHC) complexes, Cp(CO)2Mn(NHC), obtained in one step from industrially produced cymantrene, were evaluated as pre-catalysts in the hydrosilylation of carbonyl compounds under UV irradiation. Complexes with NHC ligands incorporating at least one mesityl group led to the most active and selective catalytic systems. A variety of aldehydes (13 examples) and ketones (11 examples) were efficiently reduced under mild conditions [Cp(CO)2Mn(IMes) (1 mol%), Ph 2SiH2 (1.5 equiv.), hν (350 nm), toluene, 25 °C, 1-24 h] with good functional group tolerance.
A New Method for the Reduction of Esters
Boyer, J.,Corriu, R.J.P.,Perz, R.,Poirier, M.,Reye, C.
, p. 558 - 559 (1981)
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Spanton,S.G.,Prestwich,G.D.
, p. 1921 (1982)
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Direct incorporation of hydroxy groups into isotactic polypropylene via metallocene-catalyzed copolymerization of ester group containing vinyl monomer treated with dialkylaluminum hydride and propylene
Sugimoto, Ryuichi,Matsugi, Tomoaki
, p. 1238 - 1240 (2015)
Methyl 10-undecenoate treated with 2 equivalents of diisobutylaluminum hydride was quantitatively converted into a 10-undecenoxy aluminum compound, which was successfully utilized for metallocene-catalyzed copolymerization with propylene to produce functional polypropylene with hydroxy groups in its side chains.
Manganese-Catalyzed Hydrogenation of Sclareolide to Ambradiol
Zubar, Viktoriia,Lichtenberger, Niels,Schelwies, Mathias,Oeser, Thomas,Hashmi, A. Stephen K.,Schaub, Thomas
, (2021/11/16)
The hydrogenation of (+)-Sclareolide to (?)-ambradiol catalyzed by a manganese pincer complex is reported. The hydrogenation reaction is performed with an air- and moisture-stable manganese catalyst and proceeds under relatively mild reaction conditions at low manganese and base loadings. A range of other esters could be successfully hydrogenated leading to the corresponding alcohols in good to quantitative yields using this easy-to-make catalyst. A scale-up experiment was performed leading to 99.3 % of the isolated yield of (?)-Ambradiol.
Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction
Chakraborty, Soumi,Das, Arpan,Mandal, Swadhin K.
supporting information, p. 12671 - 12674 (2021/12/04)
Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.
