39267-49-7Relevant academic research and scientific papers
Hole transport material and preparation method thereof, and electroluminescent device
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Paragraph 0048; 0053-0054, (2020/03/02)
The invention relates to a hole transport material and a preparation method thereof, and an electroluminescent device, wherein the structural formula of the hole transport material is that the designed and synthesized hole transport material has an approp
Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles
Rama, Raquel J.,Maya, Celia,Nicasio, M. Carmen
supporting information, p. 1064 - 1073 (2020/01/25)
A series of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR2Ar′ (R=Me, Et, iPr, Cyp (cyclopentyl), Ar′=ArDipp2, ArXyl2f, Dipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl=xylyl) have been prepared and structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e., Me and Et substituents) whereas the largest phosphines provided cationic palladacycles in which the phosphines adopted a bidentate hemilabile k1-P,η1-Carene coordination mode. The influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2ArXyl2 and PCyp2ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low catalyst loadings (0.25–0.75 mol % Pd) and without excess ligand.
PhPAd-DalPhos: Ligand-Enabled, Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles with Bulky Primary Alkylamines
Tassone, Joseph P.,England, Emma V.,MacQueen, Preston M.,Ferguson, Michael J.,Stradiotto, Mark
supporting information, p. 2485 - 2489 (2019/02/03)
The base metal-catalyzed C?N cross-coupling of bulky α,α,α-trisubstituted primary alkylamines with (hetero)aryl electrophiles represents a challenging and under-developed class of transformations that is of significant potential utility, including in the synthesis of lipophilic active pharmaceutical ingredients. Herein, we report that a new, air-stable Ni(II) pre-catalyst incorporating the optimized ancillary ligand PhPAd-DalPhos enables such transformations of (hetero)aryl chloride, bromide, and tosylate electrophiles to be carried out for the first time with substrate scope rivalling that achieved using state-of-the-art Pd catalysts, including room temperature cross-couplings of (hetero)aryl chlorides that are unprecedented for any catalyst (Pd, Ni, or other).
Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
Roscales, Silvia,Csák?, Aurelio G.
, p. 1667 - 1671 (2018/03/23)
The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
COLORING COMPOSITION, INKJET INK, FABRIC PRINTING METHOD, AND DYED OR PRINTED FABRIC
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Paragraph 0238; 0239; 0240, (2017/06/02)
PROBLEM TO BE SOLVED: To provide a coloring composition having excellent light resistance and excellent storage stability, inkjet ink comprising the coloring composition, a fabric printing method, and a dyed or printed fabric. SOLUTION: The present invent
NOVEL COMPOUND, COLORING COMPOSITION FOR DYEING OR TEXTILE PRINTING, INK JET INK, METHOD OF PRINTING ON FABRIC, AND DYED OR PRINTED FABRIC
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Paragraph 0350; 0351, (2017/05/10)
Provided are a compound represented by any one of Formulae (1) to (3) (for example, the following compound), a coloring composition for dyeing or textile printing including the compound, an ink jet ink including the coloring composition for dyeing or text
Flexible Steric Bulky Bis(Imino)acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Precatalysts: Catalytic Application in Buchwald-Hartwig Amination in Air
Lan, Xiao-Bing,Li, Yinwu,Li, Yan-Fang,Shen, Dong-Sheng,Ke, Zhuofeng,Liu, Feng-Shou
, p. 2914 - 2925 (2017/03/23)
To achieve efficient palladium-catalyzed cross-coupling reaction under mild reaction conditions with the flexible steric bulk strategy, a series of Pd-PEPPSI (PEPPSI: pyridine-enhanced precatalyst preparation, stabilization, and initiation) complexes C1-C6 were synthesized and characterized, in which unsymmetric flexible steric bulk was introduced on the N-aryl of ancenaphthyl skeleton. These well-defined palladium complexes were found to be excellent precatalysts for Buchwald-Hartwig amination of aryl chlorides with amines in air. The electronic effect of the Pd-PEPPSI complexes and the effect of ancillary pyridine ligands were evaluated, among which complex C3 exhibited the most efficiency. It was demonstrated that the cross-coupling products were obtained in excellent yields in the presence of 0.5-0.1 mol % palladium loading. A wide range of aryl- and heteroaryl chlorides as well as various amines were compatible. The oxidative addition of aryl chlorides is revealed to be the rate-determining step in the catalytic cycle. The catalytic activity can be enhanced by introducing electron-donating groups to the Pd-PEPPSI complexes. This type of Pd-PEPPSI precatalyst showed the most efficiency reported to date for the challenging C-N cross-coupling reactions requiring no anhydrous and inert atmosphere protections, suggesting flexible steric bulk as a promising catalyst design strategy.
Oxaphosphole-based monophosphorus ligands for palladium-catalyzed amination reactions
Rodriguez, Sonia,Qu, Bo,Haddad, Nizar,Reeves, Diana C.,Tang, Wenjun,Lee, Heewon,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
supporting information; experimental part, p. 533 - 537 (2011/04/22)
A novel class of C-2-substituted oxaphosphole-based monophosphines 1-4 has been synthesized. Palladium complexes derived from these ligands and their C-2-unsubstituted analogs provide general catalysts for amination reactions of challenging aryl and heteroaryl halides with sterically hindered anilines and alkylamines.
Synthesis and X-ray structure determination of highly active Pd(II), Pd(I), and Pd(0) complexes of Di(tert -butyl)neopentylphosphine (DTBNpP) in the arylation of amines and ketones
Hill, Lensey L.,Crowell, Jason L.,Tutwiler, Strudwick L.,Massie, Nicholas L.,Hines, C. Corey,Griffin, Scott T.,Rogers, Robin D.,Shaughnessy, Kevin H.,Grasa, Gabriela A.,Johansson Seechurn, Carin C. C.,Li, Hongbo,Colacot, Thomas J.,Chou, Joe,Woltermann, Christopher J.
supporting information; experimental part, p. 6477 - 6488 (2010/12/24)
The air-stable complex Pd(eta;3-allyl)(DTBNpP)Cl (DTBNpP = di(tert-butyl)neopentylphosphine) serves as a highly efficient precatalyst for the arylation of amines and enolates using aryl bromides and chlorides under mild conditions with yields ranging from 74% to 98%. Amination reactions of aryl bromides were carried out using 1-2 mol % Pd(η3-allyl)(DTBNpP)Cl at 23-50 °C without the need to exclude oxygen or moisture. The C-N coupling of the aryl chlorides occurred at relatively lower temperature (80-100 °C) and catalyst loading (1 mol %) using the Pd(eta;3-allyl) (DTBNpP)Cl precatalyst than the catalyst generated in situ from DTBNpP and Pd2(dba)3 (100-140 °C, 2-5 mol % Pd). Other Pd(DTBNpP)2-based complexes, (Pd(DTBNpP)2 and Pd(DTBNpP)2Cl2) were ineffective precatalysts under identical conditions for the amination reactions. Both Pd(DTBNpP)2 and Pd(DTBNpP)2Cl2 precatalysts gave nearly quantitative conversions to the product in the α-arylation of propiophenone with p-chlorotoluene and p-bromoanisole at a substrate/catalyst loading of 100/1. At lower substrate/ca'alyst loading (1000/1), the conversions were lower but comparable to that of Pd(t-Bu3P)2. In many cases, the tri-tert-butylphosphine (TTBP) based Pd(I) dimer, [Pd(μ-Br)(TTBP)] 2, stood out to be the most reactive catalyst under identical conditions for the enolate arylation. Interestingly, the air-stable Pd(I) dimer, Pd2(DTBNpP)2(μ-Cl)(μ-allyl), was less active in comparison to [Pd(μ-Br)(TTBP)]2 and Pd(eta;3-allyl) (DTBNpP)Cl. The X-ray crystal structures of Pd(eta;3-allyl)(DTBNpP) Cl, Pd(DTBNpP)2Cl2, Pd(DTBNpP)2, and Pd 2(DTBNpP)2(μ-Cl)(μ-allyl) are reported in this paper along with initial studies on the catalyst activation of the Pd(eta;3-allyl)(DTBNpP)Cl precatalyst.
P(i-BuNCH2CH2)3N: An effective ligand in the palladium-catalyzed amination of aryl bromides and iodides
Urgaonkar, Sameer,Nagarajan,Verkade
, p. 452 - 459 (2007/10/03)
It is shown that the bicyclic triaminophosphine P(i-BuNCH2CH2)3N serves as an effective ligand for the palladium-catalyzed amination of a wide array of aryl bromides and iodides. Other bicyclic or acyclic triaminophosphines, even those of similar basicity and/or bulk, were inferior.
