495-76-1Relevant articles and documents
A novel method to convert ketones and aldehydes to the corresponding alcohols
Wei-Dong, Yang,Chi, Yang,An-Xing, Wu
, p. 2827 - 2830 (1998)
A novel method of converting aldehydes and ketones to the corresponding alcohols based on selective indirective electroreduction was found, in which EtOH was used as a support electrolyte and Al(OC2H5)3 as intermedia that was produced on spot reduction by electrolysis. The reaction took place in a cell with two Al electrodes.
Degradation of the neolignan, burchellin in the hemolymph of the bloodsucking insect Rhodnius prolixus
Cabral, Marise M.O.,Garcia, Eloi S.,Gottlieb, Otto R.,Kelecom, Alphonse
, p. 59 - 63 (2008)
The neolignan, burchellin, a natural compound that reduces urine excretion in larvae of the bloodsucking bug, Rhodnius prolixus, a vector of Chagas' disease, is rapidly degraded in the hemolymph of the insect. The main product that accumulates in this tissue has been shown to be piperonyl alcohol. Other catabolites have been identified by GC-MS analysis.
Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
supporting information, p. 6648 - 6653 (2021/09/08)
The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
Iron-catalyzed chemoselective hydride transfer reactions
Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, (2021/06/07)
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: An application in furfural conversion
Gholap, Sandeep Suryabhan,Dakhil, Abdullah Al,Chakraborty, Priyanka,Li, Huaifeng,Dutta, Indranil,Das, Pradip K.,Huang, Kuo-Wei
supporting information, p. 11815 - 11818 (2021/11/30)
Well-defined and air-stable PN3-pincer manganese(ii) complexes were synthesized and used for the hydrogenation of aldehydes into alcohols under mild conditions using MeOH as a solvent. This protocol is applicable for a wide range of aldehydes containing various functional groups. Importantly, α,β-unsaturated aldehydes, including ynals, are hydrogenated with the CC double bond/CC triple bond intact. Our methodology was demonstrated for the conversion of biomass derived feedstocks such as furfural and 5-formylfurfural to furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol respectively.
Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions
Cao, Dawei,Xia, Shumei,Pan, Pan,Zeng, Huiying,Li, Chao-Jun,Peng, Yong
supporting information, p. 7539 - 7543 (2021/10/12)
Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.
Method for synthesizing piperonyl alcohol through catalytic hydrogenation
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Paragraph 0024-0035, (2021/02/10)
The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing piperonyl alcohol through catalytic hydrogenation, which comprises the followingsteps of: firstly, adding piperonal solution and Raney nickel into a hydrogenation reaction kettle according to the mass ratio of 1: (0.01-1), and introducing inert gas to replace air in the hydrogenation reaction kettle; and secondly, introducing hydrogen, heating to 30-150 DEG C, carrying out a catalytic hydrogenation reaction under the hydrogen pressure of 0.5-5 MPa, filtering to recover Raneynickel after the reaction is finished, and carrying out reduced pressure distillation on the filtrate to obtain a recovered solvent and a crude piperonyl alcohol product. According to the method, theproblems of expensive catalyst, low production efficiency and high production cost in the synthesis process of the piperonyl alcohol in the prior art are solved, the piperonal and the solvent are mixed and subjected to hydrogenation reduction to form the piperonyl alcohol at a certain pressure and temperature under the catalytic action of Raney nickel, the process yield is high, no three wastes are generated, and the method conforms to the green development trend.
Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction
Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni
supporting information, p. 2162 - 2168 (2021/04/02)
A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.
C(sp3)-H Monoarylation of Methanol Enabled by a Bidentate Auxiliary
Gou, Quan,Ran, Man,Ren, Jian,Tan, Xiaoping,Yuan, Binfang,Yuan, Tengrui,Zhang, Ming-Zhong,Zhang, Xing
supporting information, p. 118 - 123 (2021/01/13)
With the assistance of a practical directing group (COAQ), the first catalytic protocol for the palladium-catalyzed C(sp3)-H monoarylation of methanol has been developed, offering an invaluable synthesis means to establish extensive derivatives of crucial arylmethanol functional fragments. Furthermore, the gram-scale reaction, broad substrate scope, excellent functional group compatibility, and even the practical synthesis of medicines further demonstrate the usefulness of this strategy.
Cyclopentadienone iron tricarbonyl complexes-catalyzed hydrogen transfer in water
Coufourier, Sébastien,Gaillard, Sylvain,Mbaye, Mbaye Diagne,Ndiaye, Daouda,Renaud, Jean-Luc
supporting information, (2020/01/28)
The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions.
