26104-72-3Relevant academic research and scientific papers
Multidentate N-Heterocyclic Carbene Complexes of Nickel and Palladium: Structural Analysis and Catalytic Application in Mizoroki–Heck Coupling Reaction
Liu, Li-Cheng,Tzeng, Yan-Hsiang,Hung, Cheng-Hau,Lee, Hon Man
, p. 3601 - 3611 (2020/09/01)
Two series of electron-rich metal (Ni and Pd) complexes, namely a pyridine-coordinated tridentate NHC/amidate/phenoxy metal complex and a tetradentate complex bearing an extra pyridyl group, were synthesized. Two carbene moieties, imidazole-based and benzimidazole-based NHCs, were also incorporated into the ligand backbones. Seven of the new complexes were structurally characterized and comparative structural analysis revealed that the tetradentate complex with a flanking pyridyl side-arm was less distorted, leading to chelation-assisted stronger NHC coordination and hence a shorter metal–carbene bond. The catalytic activities of the two sets of palladium complexes for the Mizoroki–Heck coupling reaction were investigated. The comparative data showed that despite the higher thermal stability and the presence of the flanking hemilabile pyridyl side-arm which provided unsaturation to the metal center, the catalytic performance was slightly inferior to that of the tridentate palladium complex with a “throw-away” pyridine ligand. The tridentate palladium complex with the benzimidazole-based NHC moiety was the most effective catalyst, allowing the utilization of a range of aryl chlorides including deactivated substrates with a low 0.2 mol-% Pd loading in molten n-tetrabutylammonium bromide.
An efficient class of bis-NHC salts: Applications in Pd-catalyzed reactions under mild reaction conditions
Chiu, Chien-Cheng,Chiu, Hui-Tzu,Lee, Dong-Sheng,Lu, Ta-Jung
, p. 26407 - 26415 (2018/08/04)
This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.
SYNTHESES OF METAL HETEROCYCLIC CARBENE ENOLATES AS COUPLING REACTIONS CATALYSTS
-
Page/Page column 15; 17; 31, (2017/07/01)
The invention relates to the synthesis methods of N-heterocyclic carbene NHCE metal complexes and their catalytic activities in carbon-carbon coupling reactions.
Novel stilbene-based Fischer base analog of leuco-TAM - (2E,2′Z)-{2-(4-(E)-styrylphenyl)propane-1,3-diylidene}bis(1,3,3-trimethylindoline) - derivatives: Synthesis and structural consideration by 1D NMR and 2D NMR spectroscopy
Keum, Sam-Rok,Lim, Hyun-Woo
, p. 143 - 150 (2016/02/09)
We report the synthesis of a series of novel stilbene-based (St) Fischer base analogs of leuco-triarylmethane (LTAM) dyes by treating Fischer base with (E)-4-styrylbenzaldehyde derivatives. All St-LTAM molecules examined herein are characterized by 1D and 2D NMR. They were found to exhibit ZE configuration and isomerize to their diastereomers EE and ZZ in 2-3 h. They exhibit type I behavior of diastereomeric isomerization.
MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO
-
Page/Page column 293-294; 295-296, (2016/10/31)
This disclosure relates to the field of moiecuies having pesticida i utility against pests in Phyla Arthropoda, Moliusca, and hJematoda, processes to produce such moiecuies, intermediates used In such processes, pesticidai compositions containing such molecules, and processes of using such pesticidai compositions against such pests. These pesticidai compositions may be used, for example, as acaricldes, insecticides, miticides, moilusclcides, and nematicides. This document discloses moiecuies having the following formula ("Formula One").
Pd(II) complexes of Schiff bases and their application as catalysts in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions
Kele, Mustafa,Kele, Hülya,Emir, Duygu Melis
, p. 543 - 548 (2015/08/04)
Schiff bases of 2-(phenylthio)aniline, (C6H5)SC6H4N=CR (R=(o-CH3)(C6H5), (o-OCH3)(C6H5) or (o-CF3)(C6H5)), and their palladium complexes (PdLCl2) were synthesized. The compounds were characterized using 1H NMR and 13C NMR spectroscopy and micro analysis. Also, electrochemical properties of the ligands and Pd(II) complexes were investigated in dimethylformamide-LiClO4 solution with cyclic and square wave voltammetry techniques. The Pd(II) complexes showed both reversible and quasi-reversible processes in the -1.5 to 0.3V potential range. The synthesized Pd(II) complexes were evaluated as catalysts in Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions.
Iminophosphine palladium(II) complexes: Synthesis, characterization, and application in Heck cross-coupling reaction of aryl bromides
Yilmaz, Mustafa Kemal,Guezel, Bilgehan
, p. 529 - 536 (2014/07/07)
Palladium(II) complexes containing phosphorus and nitrogen donor atoms (iminophosphine), dichlorido{N-[2-(diphenylphosphino)benzylidene]-2- trifluoromethylaniline}palladium(II) 1, dichlorido{N-[2-(diphenylphosphino) benzylidene]-3-trifluoromethylaniline}palladium(II) 2, dichlorido{N-[2- (diphenylphosphino)benzylidene]-2-methylaniline}palladium(II) 3, dichlorido{N-[2-(diphenylphosphino)benzylidene]-3-methylaniline}palladium(II) 4 have been successfully synthesized and fully characterized by FT-IR and NMR (1H, 31P, 19F, and 13C) spectroscopy techniques. These complexes were first step tested in the reaction of bromobenzene and styrene to determine the optimal coupling reaction conditions and then successfully applied as catalysts for Heck cross-coupling reactions of activated and deactivated aryl bromides with styrene derivatives and several acrylates. Copyright
Fluorogenic probes for aldol reactions: Tuning of fluorescence using π-conjugation systems
Katsuyama, Isamu,Chouthaiwale, Pandurang V.,Akama, Hiroyuki,Cui, Hai-Lei,Tanaka, Fujie
supporting information, p. 74 - 78 (2014/01/06)
Fluorogenic aldehydes or probes for monitoring of the progress of aldol reactions have been developed. Fluorescence of benzaldehydes conjugated with aryl groups via a double or triple bond and of their aldol products was evaluated in aqueous solutions. Ba
Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts
Pavia, Cinzia,Giacalone, Francesco,Bivona, Lucia Anna,Salvo, Anna Maria Pia,Petrucci, Chiara,Strappaveccia, Giacomo,Vaccaro, Luigi,Aprile, Carmela,Gruttadauria, Michelangelo
, p. 57 - 62 (2014/04/03)
Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.
Synthesis and photoluminescent properties of conjugated aryl-vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives
Bosiak, Mariusz J.,Rakowiecki, Marcin,Or?owska, Katarzyna J.,K?dziera, Dariusz,Adams, J?rg
, p. 803 - 811 (2013/09/12)
The synthesis of highly fluorescent conjugated benzodifuran aryl-vinyl systems, containing four double bonds and at least four phenyl rings, is described. The ethyl groups of diethyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7- dicarboxylate, obtained by the Michael type condensation of p-benzoquinone and ethyl acetoacetate, were replaced by octyl groups via the transesterification reaction to improve the desired product solubility in common organic solvents. The dioctyl ester was brominated and used for the Wittig reaction with stilbene aldehydes, obtained by the Heck reaction of 4-bromobenzaldehyde and an appropriate styrene. The products, obtained in 48-92% yield, exhibit the UV-Vis fluorescence with high quantum yields, 58-69%.
