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Xue Li, Yunyun Bian, Xin Chen, Hang Zhang, Wei Wang, Sida Ren, Xuechen Yang, Chang Lu, Chunxia Chen, Jinsong Peng
An efficient sequential one-pot synthesis of fused heterocycles based on 4-quinolinone and isoquinoline scaffolds of biological interest has been developed. In all cases, the first nucleophilic addition of 2-aryl quinolin-4(1H)-ones to alkynyl bromides in tert-pentyl alcohol can proceed in a chemo-, regio- and stereoselective manner to give (Z)-N-(1-bromo-1-alken-2-yl)quinolin-4-ones at 110 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular aromatic C-H alkenylation in the presence of PdCl2 (5 mol%) in mixed solvents (tert-pentyl alcohol/DMF = 1 : 1), affording the novel quinolinone-fused isoquinoline derivatives in good yields...
December 13, 2018: Organic & Biomolecular Chemistry
Arián E Roa, Verónica Salazar, Daniel Mendoza-Espinosa, Margarita Paneque, Antonio Rodríguez-Diéguez, Ana M Rodríguez, Juan Tejeda, José A Castro-Osma, Antonio Otero, Agustín Lara-Sánchez
A new coordination mode for the hybrid scorpionate/cyclopentadienyl ligand bpzcp, [bpzcp = 2,2-bis(3,5-dimethylpyrazol-1-yl)-1,1-diphenylethylcyclopentadienyl] is observed in iridium complexes. The reaction of the lithium precursor, [Li(bpzcp)(THF)], with a range of [IrCl(diene)]2 compounds leads to an unprecedented binding mode of the hybrid scorpionate/cyclopentadienyl ligand as η5 -Cp-coordinated and the formation of Ir(I) derivatives [Ir(η5 -Cp-bpzcp)(η4 -cod)] (1), [Ir(η5 -Cp-bpzcp){η4 -CH2 ═C(Me)C(Me)═CH2 }] (2), [Ir(η5 -Cp-bpzcp)(η2 -coe)2 ] (3), and [Ir(η5 -Cp-bpzcp)(η2 -CH2 ═CH2 )2 ] (4)...
December 12, 2018: Inorganic Chemistry
Lisbeth Rosholm Comstedt, Malin Engfeldt, Cecilia Svedman, Anna Åkesson, Monica Hindsén, Magnus Bruze
Concomitant reactions to palladium chloride (PdCl2 ), sodium tetrachloropalladate (Na2 PdCl4 ), and nickel hexahydrate sulphate (NiSO4 ·6H2 O) are very common during patch testing and have mainly been explained by cross-sensitisation. Whether there is variation in reactivity to palladium or covariation to nickel and palladium is not known. The aim of this study was to investigate the variation in patch test reactivity to PdCl2 and Na2 PdCl4 over time and compare this to variation in patch test reactivity to NiSO4 ·6H2 O...
October 1, 2018: European Journal of Dermatology: EJD
Mengdie Xu, Jing Zhao, Guiqing Shu, Xiu Zheng, Qi Liu, Yudong Wang, Minfeng Zeng
Novel porous nitrogen-doped carbon supported Pd (Pd@N-C) catalytic composites were prepared by one-pot thermal carbonization of chitosan/poly(ethylene glycol)‑block‑poly(propylene glycol)‑block‑poly(ethylene glycol)/PdCl2 (CS/P123/PdCl2 ) blend hydrogel membranes at different temperature in N2 atmosphere. The porous structure of the Pd@N-C catalytic composite was governed by both the addition of P123 and the carbonization temperature. At highest carbonization temperature of 900 °C, the prepared Pd@N-C catalytic composite from CS/P123/PdCl2 blend membrane showed the highest specific area (SBET ) of 293...
December 3, 2018: International Journal of Biological Macromolecules
Tsuyoshi Mita, Sho Ishii, Yuki Higuchi, Yoshihiro Sato
By using a new catalytic system (PdCl2 [P( n-Bu)3 ]2 in combination with ZnEt2 ), various 3-indolylmethanol derivatives were successfully carboxylated with CO2 (1 atm) via dearomatization of the indole nucleus, affording 3-methyleneindoline-2-carboxylates. In contrast, carboxylation of 2-indolylmethanol derivatives afforded unexpected doubly carboxylated products, which are useful synthetic precursors for biologically active compounds.
November 26, 2018: Organic Letters
John B Coulton, Aramis C Smith, Kraig A Wheeler, Radu F Semeniuc
A new ditopic ligand, N-(2,2-bis(pyrazolyl)ethyl)-2,2-bis(pyrazolyl)acetamide ((pz)2CH-C(O)-NH-CH2-CH(pz)2, L4Pz, pz = pyrazolyl ring), comprising two bis(pyrazolyl)methane donor groups linked via an amide bridge, has been prepared from the reaction of HOOCCH(pz)2 and H2NCH2CH(pz)2. The ligand coordinates to various metallic salts (i.e. AgO3SCF3, PdCl2, Re(CO)5Br, and Fe(BF4)2), in either a κ2-μ-κ2 or a κ3-μ-κ2 fashion, depending on the coordination preferences of the metallic center. These compounds were characterized by NMR, UV-Vis and IR spectroscopy, and in solid state by single crystal X-ray diffraction...
November 22, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Yaqian Zhao, Yunxing Li, Huan Pang, Cheng Yang, To Ngai
The combination of noble metal nanoparticles (NM NPs) and metal-organic frameworks (MOFs) for enhanced properties in catalysis is a rapidly developing interdisciplinary research field. Herein we report a facile one-step approach to the deposition of functional nanocomposite shell composed of NM NPs and conducting polymer on the surface of particulate UiO-66. Our approach is based on the recently developed double solvents method involving a hydrophobic solvent (n-hexane) and a hydrophilic solvent (water). Particularly, the n-hexane was used in a large amount to suspend the UiO-66 particles with hydrophilic inner pores and promoted the enrichment of the water containing the palladium chloride (PdCl2 ) inside the pores of UiO-66 particles, because these two solvents are immiscible and the volume of water is smaller than the pore volume of the UiO-66 particles...
November 10, 2018: Journal of Colloid and Interface Science
Riku Iwasaki, Eikichi Tanaka, Toshinari Ichihashi, Yasushi Idemoto, Kohei Endo
The treatment of PdCl2 with K2 CO3 and HCO2 H in dioxane gives black precipitates, which are an effective catalyst for the semireduction of alkynes to alkenes using formic acid as a reductant. Even 0.05 mol % Pd promoted the reduction reaction of tolane in high yield with high selectivity.
November 2, 2018: Journal of Organic Chemistry
Karel Škoch, Ivana Císařová, Filip Uhlík, Petr Štěpnička
Isomeric phosphinoferrocene ligands, viz. 1'-(diphenylphosphino)-1-cyanoferrocene (1) and 1'-(diphenylphosphino)-1-isocyanoferrocene (2), show markedly different coordination behaviours. For instance, the reactions of 1 with [PdCl2(MeCN)2] and [(LNC)Pd(μ-Cl)]2 (LNC = [2-(dimethylamino-κN)methyl]phenyl-κC1) produced the "phosphine" complexes [PdCl2(1-κP)2] (7) and [(LNC)PdCl(1-κP)] (8), and the latter was converted into the coordination polymer [(LNC)Pd(μ(P,N)-1)][SbF6] (9). Conversely, the reaction of 2 with [(LNC)Pd(μ-Cl)]2 involved coordination of the phosphine moiety and simultaneous insertion of the isocyanide group into the Pd-C bond, giving rise to the P,η1-imidoyl complex [PdCl(Ph2PfcN[double bond, length as m-dash]CC6H4CH2NMe2-κ3C,N,P)] (10; fc = ferrocene-1,1'-diyl)...
November 22, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Petre Flaviu Gostin, Owen Addison, Alexander P Morrell, Yue Zhang, Angus J M C Cook, Alethea Liens, Mihai Stoica, Konstantin Ignatyev, Steven R Street, Jing Wu, Yu-Lung Chiu, Alison J Davenport
Ti-based bulk metallic glasses are under consideration for implants due to their high yield strength and biocompatibility. In this work, in situ synchrotron X-ray diffraction (XRD) is used to investigate the corrosion products formed from corrosion of Ti40 Zr10 Cu34 Pd14 Sn2 bulk metallic glass in artificial corrosion pits in physiological saline (NaCl). It is found that Pd nanoparticles form in the interior of the pits during electrochemical dissolution. At a low pit growth potential, the change in lattice parameter of the Pd nanoparticles is consistent with the formation of palladium hydride...
September 16, 2018: Advanced Healthcare Materials
Sadeeq Ullah, Aftab Ahmad, Arifullah Khan, Jie Zhang, Muslim Raza, Aziz Ur Rahman, Muhammad Tariq, Usman Ali Khan, Shah Zada, Qipeng Yuan
Low cost and an easy technique for the synthesis of palladium nanoparticles (PdNPs) was developed. Glucosamine was used to stabilize palladium precursor (PdCl2 ) into palladium nanoparticles. Several analytical techniques were used for the determination of morphology, crystalline structure; size, capping, and composition of synthesize palladium nanoparticles. The UV-visible spectroscopy SPR peak (Surface Plasmon Resonance) at 284 nm revealed synthesis of PdNPs. Energy dispersive X-ray (EDX) and X-ray diffraction (XRD) studies proved the elemental composition and crystalline structure of the synthesized palladium nanoparticles respectively...
September 12, 2018: Microbial Pathogenesis
Yasunari Monguchi, Tomohiro Ichikawa, Tsuyoshi Yamada, Yoshinari Sawama, Hironao Sajiki
Microwave-assisted continuous-flow reactions have attracted significant interest from synthetic organic chemists, especially process chemists from practical points of view, due to a less complicated shift to large-scale synthesis based on simple and continuous access to products with low energy requirements. In this personal account, we focused on the Suzuki-Miyaura and Mizoroki-Heck reactions, both of which are significantly important cross-coupling reactions for the synthesis of various functional materials...
September 4, 2018: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
Tao Zhang, Guigang Deng, Hanjie Li, Bingxin Liu, Qitao Tan, Bin Xu
A palladium-catalyzed synthesis of dibenzothiophenes from 2-biphenylthiols is described. This highly efficient reaction employs a simple PdCl2 /DMSO catalytic system, in which PdCl2 is the sole metal catalyst and DMSO functions as an oxidant and solvent. This transformation has broad substrate scope and operational simplicity and proceeds in high yield. The synthetic utility was demonstrated by the facile synthesis of helical dinapthothiophene 3 and an eminent organic semiconductor DBTDT 4. Importantly, highly strained trithiasumanene 5, a buckybowl of considerable synthetic challenge, was observed under this catalytic system...
September 7, 2018: Organic Letters
Rena Simayi, Simone M Gillbard, Warren B Cross, Eric G Hope, Kuldip Singh, Gregory A Solan
The pyridylimine-substituted 1-naphthalenes, 2-(1-C10H7)-6-{CR[double bond, length as m-dash]N(2,6-i-Pr2C6H3)}C5H3N (R = Me HLMe, H HLH), react with Na2[PdCl4] in acetic acid at elevated temperature to afford either ortho-C-Hnaphthyl activated (LMe)PdCl (2ortho) or the unactivated adduct (HLH)PdCl2 (1b). Alternatively, 1b and its ketimine analogue (HLMe)PdCl2 (1a), can be prepared by treating (MeCN)2PdCl2 with either HLMe or HLH in chloroform at room temperature. Regio-selective ortho-C-H activation to form 2ortho can also be initiated by the thermolysis of 1a in acetic acid, while no reaction occurs under similar conditions with 1b...
August 21, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Vnira Rakhimovna Akhmetova, Rozalia Akramovna Galimova, Nail Salavatovich Akhmadiev, Albina Midkhatovna Galimova, Ravil Akhmetzyanovich Khisamutdinov, Galiya Maratovna Nurtdinova, Eduard Feliksovich Agletdinov, Valery Alekseevich Kataev
Purpose: This research is devoted to designing the synthesis of sulfanyl-substituted 3,5-dimethylisoxazoles, which contain structural analogues of the SAM drug in the molecule. SAM (S-adenosyl-L-methionine), formed in the biosynthetic process, is used as an effective hepatoprotective drug. Complexation and hepatoprotective properties of the combinatorial series of bis(isoxazolylsulfanyl)ethane have been studied. Methods: Bis(isoxazol-4-ylmethylsulfanyl)alkanes were synthesized using the one-pot method. The structures of compounds were established by one-dimensional (1 H,13 C) and two-dimensional (COSY, HCQS, HMBC) NMR spectroscopy, mass-spectrometry and X-ray diffraction...
June 2018: Advanced Pharmaceutical Bulletin
Sheng Zhang, Hengmin Ma, Hon Eong Ho, Yoshinori Yamamoto, Ming Bao, Tienan Jin
A new and efficient Pd-catalyzed cascade cyclization of biaryl-tethered o-alkynylanilines for the formation of dibenzo[a,c]carbazole derivatives has been reported. The use of the alkyl-substituted tertiary anilines together with the combination of the PdCl2 catalyst with the MnO2 oxidant and PivOH is vital for giving rise to 5-endo cyclization, C-N bond cleavage, and C-H bond activation in a cascade manner to produce the corresponding products with structural diversity.
July 25, 2018: Organic & Biomolecular Chemistry
Sunit Kumar, Kishor G Thorat, Way-Zen Lee, Mangalampalli Ravikanth
A new nonaromatic selenabenziporphyrin was synthesized by (3 + 1) condensation of m-benzitripyrrane and 2,5-bis[( p-tolyl)hydroxymethyl] selenophene under mild trifluoroacetic acid-catalyzed reaction conditions. The selenabenziporphyrin was characterized by high-resolution mass spectrometry, one- and two-dimensional NMR spectroscopy, and X-ray crystallography. The crystal structure revealed that the macrocycle was planar with moderately tilted m-phenylene ring and that the phenylene ring completely blocks the macrocyclic π-delocalization...
August 6, 2018: Inorganic Chemistry
Oishi Jana, Ganesan Mani
2,6-Bis(3,5-dimethylpyrazoylmethyl)-4-methylphenol LH was readily synthesized by the reaction between 2,6-bis[(dimethylamino)methyl]-4-methylphenol and 3,5-dimethylpyrazole. The X-ray structure of the trisodium complex of LH showed the benzene-like planar Na3 O3 ring with alternative shorter (2.181-2.185 Å) and longer (2.244-2.263 Å) bonds. The reaction of anionic ligand L with [PdCl2 (COD)] yielded three Pd(II) complexes: [Pd{OC6 H2 (CH2 PzMe2 )2 -2,6-Me-4-κ N, O}2 ] (1), [PdCl{μ-OC6 H2 (CH2 PzMe2 )2 -2,6-Me-4-κ N, O, N}]2 (2), and [PdCl2 {μ-OC6 H2 (CH2 PzMe2 )2 -2,6-Me-4-κ N, O, N}2 Pd] (3) (PzMe2 = 3,5-dimethylpyrazole)...
July 2, 2018: Inorganic Chemistry
Ioannis Bratsos, Christos Tampaxis, Ioannis Spanopoulos, Nicola Demitri, Georgia Charalambopoulou, Dionisios Vourloumis, Theodore A Steriotis, Pantelis N Trikalitis
The targeted synthesis of metal-organic frameworks (MOFs) with open metal sites, following reticular chemistry rules, provides a straightforward methodology toward the development of advanced porous materials especially for gas storage/separation applications. Using a palladated tetracarboxylate metalloligand as a 4-connected node, we succeeded in synthesizing the first heterobimetallic In(III)/Pd(II)-based MOF with square-octahedron (soc) topology. The new MOF, formulated as [In3 O(L)1.5 (H2 O)2 Cl]·n(solv) (1), features the oxo-centered trinuclear clusters, [In3 (μ3 -O)(-COO)6 ], acting as trigonal-prismatic 6-connected nodes that linked together with the metalloligand trans-[PdCl2 (PDC)2 ] (L4- ) (PDC: pyridine-3,5-dicarboxylate) to form a 3D network...
June 18, 2018: Inorganic Chemistry
Pengfei Ai, Kirill Yu Monakhov, Jan van Leusen, Paul Kögerler, Christophe Gourlaouen, Moniek Tromp, Richard Welter, Andreas A Danopoulos, Pierre Braunstein
Selective copper(I) to palladium(0) transmetallation of P-donors from the rigid N,N'-diphosphanyl-imidazol-2-ylidene C3 H2 [NP(tBu)2 ]2 (PCNHC P) was observed when known [Cu3 (μ3 -PCNHC P,κP,κCNHC ,κP)2 ](OTf)3 was reacted with [Pd(PPh3 )4 ]. When 1.2 equivalents of [Pd(PPh3 )4 ] was used, the product [Cu2 Pd(μ3 -PCNHC P,κP,κCNHC ,κP)2 ](OTf)2 (2(OTf)2 ) was obtained, which features a CuI -CuI -Pd0 chain and appears to be the first linear heterotrinuclear complex with d10 -d10 interactions between Pd0 and CuI ...
June 21, 2018: Chemistry: a European Journal
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