15814-45-6Relevant academic research and scientific papers
In situ synthesis of 2-allyloxy-1-methylpyridinium triflate for the allylation of carboxylic acids
Strayer, Timothy A.,Culy, Caleb C.,Bunner, Matthew H.,Frank, Amie R.,Albiniak, Philip A.
, p. 6807 - 6809 (2015)
2-Allyloxypyridinium triflate is formed in situ by treating a mixture of 2-allyloxypyridine, a carboxylic acid, and toluene with methyl triflate. Subsequent warming of the reaction mixture in the presence of potassium carbonate leads to efficient formation of allyl esters in good to excellent yields.
Manganese-catalyzed homogeneous hydrogenation of ketones and conjugate reduction of α,β-unsaturated carboxylic acid derivatives: A chemoselective, robust, and phosphine-free in situ-protocol
Topf, Christoph,Vielhaber, Thomas
, (2021/07/10)
We communicate a user-friendly and glove-box-free catalytic protocol for the manganese-catalyzed hydrogenation of ketones and conjugated C[dbnd]C[sbnd]bonds of esters and nitriles. The respective catalyst is readily assembled in situ from the privileged [Mn(CO)5Br] precursor and cheap 2-picolylamine. The catalytic transformations were performed in the presence of t-BuOK whereby the corresponding hydrogenation products were obtained in good to excellent yields. The described system offers a brisk and atom-efficient access to both secondary alcohols and saturated esters avoiding the use of oxygen-sensitive and expensive phosphine-based ligands.
Method for selective reduction α, β - unsaturated carbonyl compound carbon-carbon double bond (by machine translation)
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Paragraph 0087-0090, (2020/06/17)
The invention discloses a method for selectively reducing carbon-carbon double bonds in α and β - unsaturated carbonyl compounds, which comprises the following steps of adding α, β - unsaturated carbonyl compounds shown in formula (I) in an electrolysis system and reducing α and β - unsaturated carbonyl compounds with carbonyl-conjugated carbon-carbon double bonds through an electrochemical cathodic reduction reaction. Compared with the reported method, the method disclosed by the invention does not use a metal catalyst and an external oxidant; and the reaction raw material and the electrolyte are low in price, nontoxic and tasteless, simple and convenient in post-treatment. (by machine translation)
Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification
?ervenková ??astná, Lucie,Bílková, Veronika,Cézová, Tereza,Cu?ínová, Petra,Karban, Jind?ich,?ermák, Jan,Krupková, Alena,Stra?ák, Tomá?
, p. 3591 - 3598 (2020/06/17)
A series of new highly fluorophilic ionic liquids (f > 110) was synthetized from 3-iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane and N-alkyl imidazoles, followed by anion exchange. N-heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification (umpolung) of cinnamaldehyde with alcohols. The most effective N-methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO2) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling.
Cobalt(II)-Catalyzed Alkoxycarbonylation of Aliphatic Amines via C-N Bond Activation
Li, Chong-Liang,Jiang, Xuan,Lu, Liang-Qiu,Xiao, Wen-Jing,Wu, Xiao-Feng
supporting information, p. 6919 - 6923 (2019/09/07)
The first cobalt-catalyzed deaminative alkoxycarbonylation reaction was described for the conversion of readily available primary alkyl amines to synthetically versatile esters with moderate to high yields. This transformation shows good functional group compatibility and can serve as a powerful tool for the modification of alkyl amine-containing complex natural products and drug molecules.
Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
supporting information, p. 5098 - 5102 (2018/09/13)
An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
Study of O-allylation using triazine-based reagents
Yamada, Kohei,Hayakawa, Naoko,Fujita, Hikaru,Kitamura, Masanori,Kunishima, Munetaka
, p. 112 - 115 (2017/01/06)
Acid-catalyzed allylating reagent 2,4,6-tris(allyloxy)-1,3,5-triazine (TriAT-allyl) and its substituted derivatives have been developed. The reaction of acid-, and alkali-labile alcohols with these reagents in the presence of a catalytic amount of trifluoromethanesulfonic acid (TfOH) afforded the corresponding allyl ethers in good yields. Reactions using these reagents with an unsymmetrically-substituted regioisometric allyl group suggested that a single isometric allylic cation species would be involved.
Simple Zn(II) Salts as Efficient Catalysts for the Homogeneous Trans-Esterification of Methyl Esters
Cucciolito, Maria E.,Lega, Matteo,Papa, Veronica,Ruffo, Francesco
, p. 1113 - 1117 (2016/06/01)
Abstract: This study aimed to optimize the zinc-catalyzed trans-esterification, and pointed to assess the effect of the solvent, the catalyst, its loading and the nature of the substrate. The screening disclosed the remarkable ability of zinc(II) acetate to promote the reaction in refluxing toluene at low catalyst loading. A significant improvement ensued with respect to recently results on the same reactions, in terms of less restrictive conditions and more convenient catalyst precursors. Graphical Abstract: [Figure not available: see fulltext.]
LED lighting as a simple, inexpensive, and sustainable alternative for Wolff rearrangements
Bernardim, Barbara,Hardman-Baldwin, Andrea M.,Burtoloso, Antonio C. B.
, p. 13311 - 13314 (2015/02/19)
The Wolff rearrangement is one of the best methods for chain homologation. However, it still suffers from many drawbacks with respect to its practical execution in the laboratory. We wish to demonstrate the use of commercial LED lamps as a sustainable alternative for the classic experimental protocols typically used for Wolff rearrangements. This journal is
Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low-Leaching and Ligand-Free Palladium Nanoparticle Catalyst
Takagi, Koji,Fukuda, Hayato,Shuto, Satoshi,Otaka, Akira,Arisawa, Mitsuhiro
supporting information, p. 2119 - 2124 (2015/06/23)
A safe, facile and low-leaching (up to 0.04ppm) method has been developed for the removal of allyl, prenyl and benzyl protecting groups from the corresponding esters, using a sulfur-modified gold-supported palladium (SAPd) nanoparticle catalyst, which is known to be non-flammable. The catalyst itself was found to be recyclable and the reaction appeared to proceed on the surface of the SAPd.
