1125-71-9Relevant academic research and scientific papers
Catalytic C1 Alkylation with Methanol and Isotope-Labeled Methanol
Sklyaruk, Jan,Borghs, Jannik C.,El-Sepelgy, Osama,Rueping, Magnus
, p. 775 - 779 (2019)
A metal-catalyzed methylation process has been developed. By employing an air- and moisture-stable manganese catalyst together with isotopically labeled methanol, a series of D-, CD3-, and 13C-labeled products were obtained in good yields under mild reaction conditions with water as the only byproduct.
One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation
Latham, Daniel E.,Polidano, Kurt,Williams, Jonathan M. J.,Morrill, Louis C.
supporting information, p. 7914 - 7918 (2019/10/16)
A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).
Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate
Swyka, Robert A.,Shuler, William G.,Spinello, Brian J.,Zhang, Wandi,Lan, Chunling,Krische, Michael J.
supporting information, p. 6864 - 6868 (2019/05/10)
A regiodivergent catalytic method for direct conversion of aldehydes to branched or linear alkyl ketones is described. Rhodium complexes modified by PtBu2Me catalyze formate-mediated aldehyde-vinyl bromide reductive coupling-redox isomerization to form branched ketones. Use of the less strongly coordinating ligand, PPh3, promotes vinyl-to allylrhodium isomerization en route to linear ketones. This method bypasses the 3-step sequence often used to convert aldehydes to ketones involving the addition of pre-metalated reagents to Weinreb or morpholine amides.
Selective hydrogenation of aromatic compounds using modified iridium nanoparticles
Jiang, He-Yan,Xu, Jie,Sun, Bin
, (2018/01/27)
Till now, Ionic liquid-stabilized metal nanoparticles were investigated as catalytic materials, mostly in the hydrogenation of simple substrates like olefins or arenes. The adjustable hydrogenation products of aromatic compounds, including quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes, are always of special interest, since they provide more choices for additional derivatization. Iridium nanoparticles (Ir NPs) were synthesized by the H2 reduction in imidazolium ionic liquid. TEM indicated that the Ir NPs is worm-like shape with the diameter around 12.2?nm and IR confirmed the modification of phosphine-functionalized ionic liquids (PFILs) to the Ir NPs. With the variation of the modifier, solvent and reaction temperature, substrate like quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes could be hydrogenated by Ir NPs with interesting adjustable catalytic activity and chemoselectivity. Ir NPs modified by PFILs are simple and efficient catalysts in challenging chemoselective hydrogenation of quinoline and relevant compounds, aromatic nitro compounds, aromatic ketones as well as aromatic aldehydes. The activity and chemoselectivity of the Ir NPs could be obviously impacted or adjusted by altering the modifier, solvent and reaction temperature.
Syndiotactic Poly(aminostyrene)-Supported Palladium Catalyst for Ketone Methylation with Methanol
Jiang, Lei,Guo, Fang,Shi, Zhenghai,Li, Yang,Hou, Zhaomin
, p. 3827 - 3832 (2017/09/25)
Palladium nanoparticles immobilized on an amino-functionalized syndiotactic polystyrene (sPS-N) served as a novel recyclable catalyst for the dimethylation and cross methyl alkylation of a wide range of ketones with methanol as the methylation agent. This heterogeneous catalyst (Pd@sPS-N) was highly robust and showed excellent thermal stability and chemical resistance. It not only showed remarkably high activity, but it could also be easily recovered by filtration without loss of activity.
Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles
Jiang, He-Yan,Zheng, Xu-Xu
, p. 3728 - 3734 (2015/07/07)
Ruthenium nanoparticles (Ru NPs) stabilized by phosphine-functionalized ionic liquids (PFILs) were synthesized in an imidazolium-based ionic liquid using H2 as a reductant. Characterization showed well-dispersed particles of about 2.2 nm (TEM) and confirmed the PFIL stabilization of the Ru NPs (NMR). The Ru NPs stabilized by PFILs exhibited excellent activity and switchable chemoselectivity in the heterogeneous selective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines under mild conditions.
Tuning the selectivity in the hydrogenation of aromatic ketones catalyzed by similar ruthenium and rhodium nanoparticles
Castelbou, Jessica Llop,Bres-Femenia, Emma,Blondeau, Pascal,Chaudret, Bruno,Castilln, Sergio,Claver, Carmen,Godard, Cyril
, p. 3160 - 3168 (2015/02/19)
Ru and Rh nanoparticles (NPs) RuI, RuII, RhI and RhII, stabilised by triphenylphosphine (PPh3) and diphenylphosphinobutane (dppb) were synthesised, characterised and applied as catalysts in the hydrogenation of several aromatic ketones. The effects of the nature of the metal and of the stabilising agent on the aryl versus ketone hydrogenation were studied. For RhNPs, the coordination of arene dominates the interaction of the substrate with the NP, whereas the coordination of the ketone group was not evidenced. For RuNPs, however, the results show that both arene and ketone coordinate to the NPs surface in a competitive manner. The properties of the stabilising ligands have a clear influence on the outcome of the reaction, and for the Rh-catalysed reactions, products of hydrogenolysis were only formed if PPh3 was used as the stabiliser. The structure of the substrate was also a key factor for the selectivity.
Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles
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Page/Page column 18, (2008/06/13)
Methods for preparing oxindole and thio-oxindole compounds are provided, which compounds are useful as precursors to useful pharmaceutical compounds. Specifically provided are methods for preparing 5-pyrrole-3,3-oxindole compounds and 5-(7-fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile. Also provided are methods for preparing iminobenzo[b]thiophene and benzo[b]thiophenone compounds.
1,1-Disilyl alcohols as d1 synthons: Harnessing the 1,2-Brook rearrangement
Fleming, Ian,Lawrence, Annabel J.,Richardson, Robert D.,Surry, David S.,West, Mark C.
, p. 3349 - 3365 (2007/10/03)
1,1-Disilyl alcohols like 6 give the silyl ethers like 9 on treatment with base and alkyl halides, in a reaction which may be formulated as the alkylation of the Brook-rearranged carbanion 8. The products can be oxidised to give ketones like 10, showing that this Brook-rearranging system supplies a controlled d1 synthon of the acyl anion class. The alcohols can be prepared from the acid chloride 12 and dimethyl(phenyl)silyllithium, but the intermediate anion 21 need not be worked up; it can be used directly in the alkylation step.
α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. I. A Novel Synthesis of Dialkyl Ketones and a Synthesis of Aldehydes from Ketones by One Carbon Elongation
Satoh, Tsuyoshi,Kaneko, Youhei,Izawa, Takao,Sakata, Kiichi,Yamakawa, Koji
, p. 1983 - 1990 (2007/10/02)
Treatment of α,β-epoxy sulfoxides, prepared from 1-chloroalkyl phenyl sulfoxides with ketones or aldehydes, with sodium benzeneselenolate gives dialkyl ketones or aldehydes in good yields under mild conditions.The mechanism of this reaction and an application of this process to a formal total synthesis of dihydrojasmone are described.
