1568-66-7Relevant academic research and scientific papers
Improved protocols for molybdenum- und tungsten-catalyzed hydrostannations
Wesquet, Alexander O.,Kazmaier, Uli
, p. 1395 - 1404 (2009)
A series of (isonitrile)tungsten carbonyl complexes of type W(CO) m(CNR)n has been synthesized and evaluated as hydrostannation catalysts. The results are compared with those obtained by the previously reported tri(tert-butylisonitri
Parameters affecting the microwave-specific acceleration of a chemical reaction
Chen, Po-Kai,Rosana, Michael R.,Dudley, Gregory B.,Stiegman
, p. 7425 - 7436 (2014)
Under appropriate conditions, significant microwave-specific enhancement of the reaction rate of an organic chemical reaction can be observed. Specifically, the unimolecular Claisen rearrangement of allyl p-nitrophenyl ether (ApNE) dissolved in naphthalen
Palladium-Catalyzed Double-Decarboxylative Addition to Pyrones: Synthesis of Conjugated Dienoic Esters
Maji, Tapan,Tunge, Jon A.
, p. 4766 - 4769 (2015)
An interceptive decarboxylative allylation protocol has been developed utilizing pyrone as a C4 synthon. This palladium-catalyzed transformation difunctionalizes the pyrone moiety by in situ generation and activation of both the electrophile and nucleophi
Determination on temperature gradient of different polar reactants in reaction mixture under microwave irradiation with molecular probe
Li, Xinhao,Xu, Jiaxi
, p. 5515 - 5520 (2016)
Temperature accurate measurement is one of key issues in illustration of the rate increase in the microwave-promoted organic reactions because reaction rates are closely related with reaction temperature. The use of molecular probe is reported as a tool to identify the microwave selective heating effects in homogenous reaction mixture of intramolecular aromatic Claisen rearrangement. Our results show direct evidence for localized superheating of polar reactants in nonpolar solvent. While in the polar solvent, the microwave selective heating effects of polar reactants will be decreased.
Pyrene-Tagged Alcoholic Ionic Liquids as Phase Transfer Catalysts for Nucleophilic Fluorination
Taher, Abu,Kim, Dong Wook
, p. 1140 - 1146 (2020)
Functional group?activity relationships of pyrene-tagged ionic liquid (PTIL)-based organocatalysts for nucleophilic fluorination using alkali metal fluorides (MFs) are described, which demonstrate that the pyrene, oligoether and alcohol moieties on the imidazolium ring are vital for efficient catalysis. Further investigation of these findings led to the discovery of new strategy, which showed superior catalyst separation process, i.e., catalyst is effortlessly separated from the reaction mixture using reduced graphene oxide. The catalytic efficiency of the PTIL as a phase transfer catalyst was demonstrated by the high conversion of the reactants up to 98% fluorinated yield using MFs in CH3CN or t-amyl alcohol. Importantly, the catalyst not only enhanced the reactivity of bimolecular nucleophilic substitutions (SN2) within a short reaction time and reduces the formation of by-products but also affords high yield with easy isolation and separation under mild conditions.
Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes
Li, Gang,Yang, Liu,Liu, Jian-Jun,Zhang, Wei,Cao, Rui,Wang, Chao,Zhang, Zunting,Xiao, Jianliang,Xue, Dong
supporting information, p. 5230 - 5234 (2021/02/05)
A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.
Aluminium chloride-potassium iodide-acetonitrile system: A mild reagent system for aromatic claisen rearrangement at ambient temperature
Bhattacharyya, Nayan Kamal,Dutta, Deepjyoti,Biswas, Joydeep
, (2021/06/28)
Claisen rearrangement is used as the standard methods for the generation of complex organic substance. It is one of the well-known methods for the introduction of carbon-carbon bond. We have developed a protocol using allyl aryl ether as a substrate and AlCl3-KI as a mild reagent system and acetonitrile (CH3CN) is taken as solvent at ambient temperature. The reagent system presented in this current work is found to be appropriate for Claisen rearrangement of several aromatic alcohols with excellent yields.
Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors
Alavi, Seyed Jamal,Seyedi, Seyed Mohammad,Saberi, Satar,Safdari, Hadi,Eshghi, Hossein,Sadeghian, Hamid
, p. 259 - 266 (2020/10/12)
In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).
Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions
Ando, Shin,Tsuzaki, Marina,Ishizuka, Tadao
, p. 11181 - 11189 (2020/10/12)
In this study, mild conditions for aromatic substitutions during the syntheses of aryl ethers were developed. In the reaction conditions, the choices of solvent, base, and the sequence for the addition of the reagents proved important. A wide variety of alcohols were used directly as nucleophiles and smoothly reacted with aryl chlorides that possessed either a nitro or a cyano group at either the ortho- or para-position. Controlled experiments we performed suggested that the reaction underwent a charge-transfer process mediated by a combination of DMF and tert-BuOK.
Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates
Hui, Zi,Jiang, Songwei,Qi, Xiang,Ye, Xiang-Yang,Xie, Tian
supporting information, (2020/05/18)
The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.
