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6380-23-0Relevant academic research and scientific papers
Cathodic Regioselective Coupling of Unactivated Aliphatic Ketones with Alkenes
Wu, Hongting,Chen, Weihao,Deng, Weijie,Yang, Ling,Li, Xinling,Hu, Yunfei,Li, Yibiao,Chen, Lu,Huang, Yubing
supporting information, p. 1412 - 1417 (2022/02/23)
A regioselective coupling of aliphatic ketones with alkenes has been realized by cathodic reduction. This reaction enables the formation of ketyl radicals and the activation of challenging alkenes under mild electrolysis conditions, providing an effective protocol for accessing diverse tertiary alcohols with substrate-dependent regioselectivity. The practicability of this reaction is demonstrated by scale-up experiments. The hydrogen source for the products, the migration isomerization of allylarenes, and the applicability of internal alkenes are demonstrated by control experiments.
Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes
Stanley, Levi M.,Tran, Hai N.
supporting information, (2021/12/27)
The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.
Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones
Dong, Guangbin,Xu, Yan,Zhou, Xukai
supporting information, p. 20042 - 20048 (2021/12/03)
The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.
Efficient synthesis of styrene derivatives through ethenolysis of renewable propenylbenzenes
Avenda?o Villarreal, Jesus A.,Delolo, Fábio G.,Granato, Artur V.,dos Santos, Eduardo N.
, (2021/06/03)
Functionalized styrenes were obtained by the ethenolysis of renewable 1-propenylbenzenes in a very efficient synthetic pathway. Some of the products are valuable food & flavor ingredients (4-vinylguaiacol) or locust pheromone (4-vinylanisole). The catalysts employed were ruthenium-alkylidene complexes bearing a N-heterocyclic carbene as a ligand, which bulkiness proved to be important for the catalysis output. The judicious choice the reaction conditions was critical to enable near quantitative yields under mild conditions in short reaction times. More strikingly, the catalyst load could be reduced to 0.01 mol%, keeping good conversion and selectivity.
The first one-pot metathesis-hydroformylation procedure: a straight synthesis of 2-arylpropanals from renewable 1-propenylbenzenes
Avenda?o Villarreal, Jesus Alberto,Delolo, Fábio Godoy,Granato, Artur Vicari,Gusevskaya, Elena Vitalievna,dos Santos, Eduardo Nicolau
, p. 8007 - 8013 (2021/12/27)
Hydroformylation is a consolidated synthetic tool in the chemical industry, both in commodity and in the fine chemicals industry. Olefin metathesis has been largely employed in the petrochemical sector, and, more recently, in the synthesis of specialty chemicals. Although these reactions may be involved in the same synthetic route for various industrial chemicals, to the best of our knowledge, they have never been combined in a one-pot procedure. As a proof of concept, we have demonstrated in the present work that the ruthenium-catalyzed ethenolysis of renewable 1-propenylbenzenes followed by the rhodium-catalyzed hydroformylation of functionalized styrenes formed in the first step could be done in one pot. The integration of these reactions was not straightforward once the catalyst of the first step interfered with the catalyst of the second step. Under optimized conditions, it was possible to synthesize 2-arylpropanals, a class of compounds valuable as synthetic intermediates to access non-steroidal anti-inflammatory drugs, in overall yields of 85-90%, at low catalyst loadings.
Ruthenium catalyzed synthesis method of primary amine
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Paragraph 0049-0052; 0055-0056, (2020/03/09)
The invention belongs to the field of organic synthesis, and discloses a ruthenium catalyzed synthesis method of primary amine. A ruthenium complex is taken as a catalyst; and a compound (A) and a compound (B) carry out reactions to obtain a compound (C); wherein R1 represents hydrogen or an alkyl group; R2 represents hydrogen or an alkyl group; R3 represent hydrogen, an alkyl group, or a phenyl group; R4 represent one of following structures shown in the description; n represents 0, 1, 2, or 3; R5 represents an alkyl group, an alkoxyl group, an ester group, a phenyl group, or a halogen atom,when n>=2, at least two R5(s) can be identical or different, m represents 0, 1, 2, or 3, R6 represents an alkyl group, an alkoxyl group, an ester group, or a halogen atom, and when m>=2, at least twoR6(s) can be identical or different. The method has the advantages of simple operation, mild conditions, small using amount of catalysts, wide substrate application range, no need of inert gas, and high yield.
Methoxy-enriched cationic stilbenes as anticancer therapeutics
Adhikari, Susanta Sekhar,Banerjee, Rajkumar,Jinka, Sudhakar,Yousuf, Md
, (2020/03/13)
Stilbene-based compounds are largely described for their antioxidant activity. But their use as anticancer chemotherapeutics is hampered by poor pharmacokinetic properties and non-selectivity towards cancer and non-cancer potency. To overcome these drawbacks, twin chain cationic lipid conjugated, methoxy-enriched stilbene derivatives were designed, synthesized and evaluated for their anticancer potency. Our findings reveal that HMSC16, a molecule with the highest number of methoxy groups and with C16-twin chain lipid, is the most potent as well as the most selective anticancer agent when compared to the other synthesized derivatives and commercially available stilbene-based drug, tamoxifen, and resveratrol. To justify these results, we have conducted a series of mechanistic experiments where we found that HMSC16 induced ROS generation, apoptosis, and autophagy by affecting the mitochondrial, lysosomal and nuclear pathways. Further cell cycle analysis data reveals that HMSC16 not only induces cell death but is also involved in the arrest of the cell cycle at the sub-G1 phase. Moreover, HMSC16 showed self-aggregation property owing to a possibly favorable hydrophilic-lipophilic balance. The self-aggregation property of HMSC16 allowed it to entrap hydrophobic drugs, withaferin. With entrapped withaferin, HMSC16 showed additive if not synergistic cell killing effect in HeLa cells. From the above results, we concluded that HMSC16 can be used not just as a drug but also as a drug delivery agent.
Hydrothermal Liquefaction of α-O-4 Aryl Ether Linkages in Lignin
Lui, Matthew Y.,Chan, Bun,Yuen, Alexander K. L.,Masters, Anthony F.,Maschmeyer, Thomas
, p. 2002 - 2006 (2020/03/05)
By using lignin model compounds with relevant key characteristic structural features, the reaction pathways of α-O-4 aryl ether linkages under hydrothermal conditions are elucidated. Experimental results and computational modeling suggest that the α-O-4 linkages in lignin undergo catalyzed hydrolysis and elimination to give phenolic and alkenylbenzene derivatives as major products in subcritical water. The decreased relative permittivity of water at these high temperatures and pressures facilitates the elimination reactions. The alkyl group on the α-carbon and the methoxy groups on the phenyl rings both have positive effects on the rate of conversion of α-O-4 linkages in native lignin.
Br?nsted Acid Catalyzed Peterson Olefinations
Britten, Thomas K.,McLaughlin, Mark G.
, p. 301 - 305 (2019/12/25)
A mild and facile Peterson olefination has been developed employing low catalyst loading of the Br?nsted acid HNTf2. The reactions are typically performed at room temperature, with the reaction tolerant to a range of useful functionalities. Furthermore, we have extended this methodology to the synthesis of enynes.
Iron-Catalyzed Direct Julia-Type Olefination of Alcohols
Landge, Vinod G.,Babu, Reshma,Yadav, Vinita,Subaramanian, Murugan,Gupta, Virendrakumar,Balaraman, Ekambaram
, p. 9876 - 9886 (2020/09/03)
Herein, we report an iron-catalyzed, convenient, and expedient strategy for the synthesis of styrene and naphthalene derivatives with the liberation of dihydrogen. The use of a catalyst derived from an earth-abundant metal provides a sustainable strategy to olefins. This method exhibits wide substrate scope (primary and secondary alcohols) functional group tolerance (amino, nitro, halo, alkoxy, thiomethoxy, and S- A nd N-heterocyclic compounds) that can be scaled up. The unprecedented synthesis of 1-methyl naphthalenes proceeds via tandem methenylation/double dehydrogenation. Mechanistic study shows that the cleavage of the C-H bond of alcohol is the rate-determining step.
