98288-15-4Relevant academic research and scientific papers
Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction
Yasukata, Tatsuro,Matsuura, Takaharu
, p. 527 - 533 (2021/03/22)
Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.
2-Phenylcyclopropylmethylamine Derivatives as Dopamine D2Receptor Partial Agonists: Design, Synthesis, and Biological Evaluation
Cheng, Jianjun,Fan, Luyu,Liu, Ruiquan,Tan, Liang,Wang, Huan,Wang, Sheng,Yan, Wenzhong,Yu, Jing
, p. 17239 - 17258 (2021/12/06)
Partial agonist activity at the dopamine D2 receptor (D2R) is the primary pharmacological feature of the third-generation antipsychotics─aripiprazole, brexpiprazole, and cariprazine. However, all these drugs share a common phenyl-piperazine moiety as the primary pharmacophore. In this study, we designed and synthesized a series of novel compounds based on the 2-phenylcyclopropylmethylamine (PCPMA) scaffold and studied their pharmacological activity at the D2R. A number of potent D2R partial agonists were identified through binding affinity screening and functional activity profiling in both G protein and β-arrestin assays. The structure-functional activity relationship results showed that the spacer group is crucial for fine-tuning the intrinsic activity of these compounds. Compounds (+)-14j and (+)-14l showed good pharmacokinetic properties and an unexpected selectivity against the serotonin 2A (5-HT2A) receptor. Preliminary suppressive effects in a mouse hyperlocomotion model proved that these PCPMA-derived D2R partial agonists are effective as potential novel antipsychotics.
Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.
supporting information, p. 558 - 564 (2020/12/07)
Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).
A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Smith, Emily G.,Cambeiro, Xacobe C.
supporting information, p. 5383 - 5388 (2021/07/26)
A photocatalytic method for the α-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the β-position. Simple scale-up is demonstrated under continuous flow conditions, highlighting the practicality of the method.
C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles
Patra, Debabrata,Panja, Subir,Saha, Amit
supporting information, p. 878 - 883 (2020/02/13)
Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.
Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers
Fu, Manlin,Liu, Jiang,Wang, Lei,Yin, Biao,Zhu, Qing
supporting information, p. 3293 - 3296 (2020/04/02)
Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected C-H alkenylation of aryl ethers promoted by a dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkenylation of alkyl aryl ethers (anisole, phenetole, n-propyl phenyl ether, n-butyl phenyl ether and benzyl phenyl ether), cyclic aryl ethers (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), and diphenyl oxides. Moreover, the proposed methodology was successfully employed for the late-stage modification of complex drugs containing the aryl ether motif. Interestingly, the compounds developed herein displayed fluorescent properties, which would facilitate their biological applications.
Finely dispersed palladium on silk-fibroin as an efficient and ligand-free catalyst for Heck cross-coupling reaction
Mirzaei, Hakimeh,Eshghi, Hossein,Seyedi, Seyed Mohammad
, (2019/09/12)
A palladium–fibroin complex (Pd/Fib.) was prepared by the addition of sonicated fibroin fiber in water to palladium acetate solution. Pd (OAc)2 was absorbed by fibroin and reduced with NaBH4 at room temperature to the Pd(0) nanoparticles. Powder-X-ray diffraction, scanning electron microscopy–energy-dispersive X-ray spectroscopy, Fourier transform-infrared, CHN elemental analysis and inductively coupled plasma-atomic emission spectroscopy were carried out to characterize the Pd/Fib. catalyst. Catalytic activity of this finely dispersed palladium was examined in the Heck coupling reaction. The catalytic coupling of aryl halides (-Cl, -Br, -I) and olefins led to the formation of the corresponding coupled products in moderate to high yields under air atmosphere. A variety of substrates, including electron-rich and electron-poor aryl halides, were converted smoothly to the targeted products in simple procedure. Heterogeneous supported Pd catalyst can be recycled and reused several times.
Bis(pyrazolyl)palladium(II) complexes as catalysts for Mizoroki–Heck cross-coupling reactions
Ocansey, Edward,Darkwa, James,Makhubela, Banothile C.E.
, p. 52 - 59 (2019/04/10)
Recent progress in carbon–carbon cross-coupling reactions has resulted in the discovery of highly active catalysts for carrying out such transformations. However, due to the wide array of applications of the products from cross-coupling reactions, there is the need to design suitable catalysts that permit the practical and economical synthesis of the cross-coupled products. Palladium complexes with bulky and electron-donating ligands have served as excellent (pre)catalysts for the Mizoroki–Heck cross-coupling reaction. By using bulky pyrazole-based ligands, we have prepared palladium(II) complexes with controlled steric and electronic properties of the metal center. We have used these bulky bis(pyrazolyl)palladium(II) complexes as (pre)catalysts for the Mizoroki–Heck cross-coupling reaction. The (pre)catalysts displayed high activity and selectivity, giving high catalytic conversions at a low (pre)catalyst loading and short reaction times. A mercury poisoning test confirmed that the (pre)catalysts promoted the Mizoroki–Heck cross-coupling homogenously and do not decompose into palladium black during the reactions. The catalytic systems were also tolerant to the presence of functional groups, such as 4-CF3, 4-CH3, 4-CO2Me and 4-CO2Et, on the alkene substrates.
Magnetic dendritic polymer nanocomposites as supports for palladium: A highly efficient and reusable catalyst for Mizoroki-Heck and Suzuki-Miyaura coupling reactions
Ma, Rong,Yang, Pengbo,Bian, Fengling
, p. 4748 - 4756 (2018/03/21)
A novel catalyst Fe3O4@SiO2-Dendrimer-Pd based on palladium immobilized on magnetic dendritic polymer nanocomposites was successfully synthesized and characterized by FT-IR, EA, XRD, TEM, EDX, VSM and XPS. This nanocatalyst showed excellent catalytic activity for solvent-free Mizoroki-Heck reaction and Suzuki-Miyaura reaction in EtOH/H2O at a palladium loading of only 0.009 mol%. Moreover, the Fe3O4@SiO2-Dendrimer-Pd catalyst could be conveniently recovered by an external magnet and used consecutively five times with excellent yields. The remarkable catalytic performances and convenient magnetic separability of the Fe3O4@SiO2-Dendrimer-Pd catalyst make it promising for practical application.
Kryptofix 5 as an inexpensive and efficient ligand for the palladium-catalyzed Mizoroki-Heck reaction
Movassagh, Barahman,Ranjbari, Shabnam
, (2018/01/27)
A novel complex of PdCl2 with a multidentate cryptand ligand, Kryptofix 5, has been prepared and characterized by various techniques including 1H- and 13C NMR spectroscopy, Fourier transform infrared (FT-IR), Raman, ultraviolet and visible (UV-VIS) spectroscopy, inductively coupled plasma (ICP), CHN elemental and energy dispersive X-ray analysis (EDX). This heat- and air-stable complex was utilized as a highly active catalyst for the Mizoroki-Heck reaction of aryl halides with various olefins. Interestingly, it was found that aryl bromides as well as aryl iodides were efficiently cross-coupled with terminal alkenes at 130?°C in 10?min. Furthermore, the least reactive aryl chlorides reacted with styrene to obtain the desired products in acceptable yields.
