112-43-6Relevant academic research and scientific papers
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.
Titanium-mediated formation of 1,2-disubstituted cyclopropanols from esters and alkenes. A new approach to the synthesis of 3,11- dimethylnonacosan-2-one, a sex pheromone of the german cockroach
Epstein, Oleg L.,Kulinkovich, Oleg G.
, p. 1823 - 1826 (1998)
A convenient new approach to the synthesis of 3,11-dimethylnonacosan-2- one (1), a component of the sex pheromone of the German cockroach Blattella germanica, using base-induced ring opening of corresponding easily available 1,2-disubstituted cyclopropanols has been performed.
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
Selective conversion of enol ethers into alcohols in the presence of alkenes using Hg(OAc)2-NaBH4
Crouch, R. David,Mehlmann, John F.,Herb, Brian R.,Mitten, Jeffrey V.,Dai, H. George
, p. 559 - 561 (1999)
Alkyl enol ethers derived from aldehydes undergo selective oxymercuration-demercuration with aqueous Hg(OAc)2-NaBH4 in the presence of an alkene in good to excellent yield. This method allows the survival of mono-, trans and cis di-, and tri-substituted alkenes as well as cyclic alkenes.
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.
Transfer-hydrogenation reactions of ketones/aldehydes in water using first generation ruthenium indenylidene olefin metathesis catalyst: One step towards sequential cross-metathesis/transfer hydrogenation reactions
?ztürk, Bengi ?zgün,?ztürk, Sinem
, (2020)
The transfer hydrogenation reactions of various ketones/aldehydes and one-pot cross-metathesis/transfer hydrogenation (CM/TH) reactions of 10-undecenal were carried out in water media using first generation ruthenium-indenylidene complex (M1). A stable emulsion with an average particle size of 23.00 (±7.20) nm was formed in water media using non-ionic (Tween 20) and cationic (dodecyltrimethylammonium chloride) surfactants in the presence of acetophenone, M1 (1%) and sodium formate, yielding corresponding alcohol derivatives in quantitative yields. The performance of M1 (5%) was tested on sequential cross-metathesis/transfer hydrogenation reaction of 10-undecenal using methyl acrylate as the cross-metathesis partner in water. The sequential CM/TH reaction of 10-undecenal was found to proceed even in tap water under air atmosphere using micellar catalyst system, giving the corresponding CM/TH product in 65% yield.
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.
REDUCTION OF ACID CHLORIDES WITH SODIUM BOROHYDRIDE IN N,N-DIMETHYLFORMAMIDE: NATURE OF THE REACTION INTERMEDIATE AND A METHOD FOR ITS CONVERSION TO THE CORRESPONDING ALDEHYDE WITH MINIMAL ALCOHOL FORMATION
Babler, James H.,Invergo, Benedict J.
, p. 11 - 14 (1981)
By use of sodium borohydride under the proper reaction conditions, direct conversion of both aliphatic and aromatic acid chlorides to the corresponding aldehyde can be achieved in 80-95percent yield.
Cationic lipids bearing succinic-based, acyclic and macrocyclic hydrophobic domains: Synthetic studies and in vitro gene transfer
Jubeli, Emile,Maginty, Amanda B.,Khalique, Nada Abdul,Raju, Liji,Nicholson, David G.,Larsen, Helge,Pungente, Michael D.,Goldring, William P.D.
, p. 225 - 232 (2017)
In this communication we describe the construction of four succinic-based cationic lipids, their formulation with plasmid DNA (pDNA), and an evaluation of their in vitro gene delivery into Chinese hamster ovarian (CHO-K1) cells. The cationic lipids employed in this work possess either a dimethylamine or trimethylamine headgroup, and a macrocyclic or an acyclic hydrophobic domain composed of, or derived from two 16-atom, succinic-based acyl chains. The synthesized lipids and a co-lipid of neutral charge, either cholesterol or 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE), were formulated in an overall 3:2 cationic-to-neutral lipid molar ratio, then complexed with plasmid DNA (pDNA). The relative transfection performance was evaluated via a comparison between matched versus mismatched formulations defined by the rigidity relationship between the lipids employed. Gel electrophoresis was used to characterize the binding of the lipid formulations with plasmid DNA and the relative degree of plasmid degradation using a DNase I degradation assay. Small angle X-ray diffraction (SAXD) was employed to characterize the packing morphology of the lipid-DNA complexes. In general, the succinic unit embedded within the hydrophobic domain of the cationic lipids was found to improve lipid hydration. The transfection assays revealed a general trend in which mismatched formulations that employed a rigid lipid combined with a non-rigid (or flexible) lipid, outperformed the matched formulations. The results from this work suggest that the design of the cationic lipid structure and the composition of the lipoplex formulation play key roles in governing the transfection performance of nonviral gene delivery agents.
