- Copper(I)-anilide complex [Na(phen)3][Cu(NPh2) 2]: An intermediate in the copper-catalyzed N-Arylation of N-Phenylaniline
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Complex [Na(phen)3][Cu(NPh2)2] (2), containing a linear bis(N-phenylanilide)copper(I) anion and a distorted octahedral tris(1,10-phenanthroline)sodium counter cation, has been isolated from the catalytic C-N cross-coupling reaction with the CuI/phen/tBuONa (phen=1,10-phenanthroline) catalytic system. Complex 2 can react with 4-iodotoluene to produce 4-methyl-N,N-diphenylaniline (3a) with 70.6% yield. In addition, 2 can work as an effective catalyst for Ci￡N coupling under the same reaction conditions, thus indicating that 2 is the intermediate of the catalytic system. Both [Cu(NPh2) 2]- and [Cu(NPh2)I]- have been observed by in situ electron ionization mass spectrometry (ESI-MS) under catalytic reaction conditions, thus confirming that they are intermediates in the reaction. A catalytic cycle has been proposed based on these observations. The molecular structure of 2 has been determined by single-crystal X-ray diffraction analysis.
- Tseng, Chia-Kai,Lee, Chi-Rung,Han, Chien-Chung,Shyu, Shin-Guang
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Read Online
- Amination and amidation of aryl iodides catalyzed by copper(I)- phenanthroline complexes
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Four kinds of copper(I)-phenanthroline complexes ([CuI(phen) 2]Cl, [CuI(phen)Cl]2, [CuI(phen) 2]BF4, and CuI(phen)PPh3Cl) were prepared and used as catalysts for amination and amidation of aryl iodide to investigate the influence on the yields of products due to differences of the structures. These complexes were found to work as catalysts on these reactions and showed that the differences of structures of copper(I) complexes significantly influenced the yield of aryl-nitrogen bond forming processes.
- Moriwaki, Kazuyuki,Satoh, Kazuyoshi,Takada, Masahiro,Ishino, Yoshio,Ohno, Toshinobu
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Read Online
- Heterogeneously Catalyzed Selective Decarbonylation of Aldehydes by CeO2-Supported Highly Dispersed Non-Electron-Rich Ni(0) Nanospecies
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Aldehyde decarbonylation has been extensively investigated, primarily using noble-metal catalysts; however, nonprecious-base-metal-catalyzed aldehyde decarbonylation has been hardly reported. We have established an efficient selective aldehyde decarbonylation reaction with a broad substrate scope and functional group tolerance utilizing a heterogeneous Ni(0) nanospecies catalyst supported on CeO2. The high catalytic performance is attributable to the highly dispersed and non-electron-rich Ni(0) nanospecies, which possibly suppress a side reaction producing esters and adsorbed CO-derived inhibition of the catalytic turnover, according to detailed catalyst characterization and kinetic evaluation.
- Matsuyama, Takehiro,Yatabe, Takafumi,Yabe, Tomohiro,Yamaguchi, Kazuya
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p. 13745 - 13751
(2021/11/17)
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- Design and synthesis of efficient electrogenerated chemiluminescent emitters derived from pyrene
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The design and synthesis of novel dendrimeric structures derived from a pyrene core with substituted triphenylamine and carbazole periphery demonstrated how molecular engineering allowed the fine tuning of the electrogenerated chemiluminiscence (ECL) properties. These two compound (Py-CBZ and Py-TPA) in comparison with the parent structures (Py and Py-Core) showed better chemical stability and anti-aggregation capability. At the same time, the photophysical (Absλmax, E00FLλmaxΦFL), photochemical (oxygen quenching), electrochemical (redox potentials) and optoelectronic (HOMO-LUMO gap and their energy position) properties were modulated, resulting in obtaining two highly ECL emitting molecular structures (Py-CBZ and Py-TPA). This study showed that functionalization of organic dyes with redox moieties (with the proper linker and position) improved the radical stability and also, modulated the optoelectronic properties with the concomitant enhancement of the ECL performance and their potential use in applications such as organic light-emitting devices.
- Cappellari, Maria V.,Mangione, María I.,Spanevello, Rolando A.,Marzari, Gabriela,Morales, Gustavo M.,Fungo, Fernando
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p. G163 - G170
(2019/05/21)
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- PdCl2(Ph3P)2/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
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Triphenylphosphine and salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o-xylene, PdCl2(Ph3P)2 with 2,5-ditrifluoromethyl N-phenylsalicylaldimine as a coligand shows high efficiency for the diarylation of various anilines. The catalytic system shows good toleration for the steric hindrance of the substrates. The facile catalytic system works as well on the multiple arylation of 1,1′-biphenyl- 4,4′-diamine with aryl chlorides to afford N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′-diamines which are important intermediates of organic light emitting diode (OLED) hole transport materials.
- Tao, Xiaochun,Li, Lei,Zhou, Yu,Qian, Xuanying,Zhao, Min,Cai, Liangzhen,Xie, Xiaomin
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supporting information
p. 1749 - 1754
(2017/10/06)
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- Donor and acceptor substituted triphenylamines exhibiting bipolar charge-transporting and NLO properties
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Donor-acceptor type triphenylamine-based malonodinitriles were synthesized and their thermal, optical, photophysical, electrochemical and nonlinear optical properties were studied. The synthesized compounds formed glasses with the glass transition temperatures ranging from 38 to 107 °C. The ionization potentials of the samples of the compounds established by cyclic voltammetry were found to be in the range of 5.50–5.57 eV, while those estimated by photoelectron emission spectrometry ranged from 5.36 to 5.74 eV. The electron affinity values of the compounds were found to be in the range of ?3.41–?3.05 eV. The ambipolar charge-transporting properties were observed for the layers of triphenylamine-based malonodinitriles. Hole mobilities of the layers of the compounds were in the range of 10?7–10?6 cm2/V·s, while electron mobilities were by ca. two orders of magnitude higher. All the synthesized compounds had positive sign for second order hyperpolarizability.
- Gudeika, Dalius,Bundulis, Arturs,Mihailovs, Igors,Volyniuk, Dmytro,Rutkis, Martins,Grazulevicius, Juozas V.
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p. 431 - 440
(2017/02/10)
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- N/O-doped carbon as a "solid ligand" for nano-Pd catalyzed biphenyl- and triphenylamine syntheses
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A series of N/O-doped porous carbon supported nanopalladium catalysts have been successfully prepared, in which the N/O doped carbons were controllably produced via polypyrrole/furan synthesis followed by carbonization. These catalysts exhibit good performance in biphenylamine and triphenylamine syntheses with nitrobenzene and cyclohexanone as starting materials. Their catalytic activity can be tuned efficiently by the N/O functional groups on the carbon surface. TEM, XRD, XPS and laser Raman methods were applied to probe the structure of these catalysts. These results indicate that the Pd nanoparticles were supported on N/O-doped porous carbon via the "coordination" between Pd nanoparticles and N/O functional groups including O-CO, CN and tertiary nitrogen, and better catalytic performance was obtained if carbon with the highest N-species loading was used as the support. In addition, a mechanistic study proved that the reaction starts with the catalytic reduction of nitrobenzene with cyclohexanone as the hydrogen source. During this reaction, aniline was formed and the cyclohexanone was transformed into phenol. Then biphenylamine and triphenylamine were generated through the reaction of aniline and cyclohexanone. This work should facilitate the controllable preparation of carbon supported nanocatalysts with specific activity, and open up a promising pathway for the development of new methodologies for N-containing fine chemical synthesis.
- Pang, Shaofeng,Zhang, Yujing,Huang, Yongji,Yuan, Hangkong,Shi, Feng
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p. 2170 - 2182
(2017/07/24)
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- Synthesis of Triarylamines via Sequential C-N Bond Formation
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A one-pot domino N-arylation protocol is described using diaryliodonium reagents under copper catalysis. The reaction uses both aryl groups of the diaryliodonium reagent to generate triarylamines starting from simple anilines, representing an atom-economical preparation of an important class of organic material building blocks.
- Modha, Sachin G.,Popescu, Mihai V.,Greaney, Michael F.
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p. 11933 - 11938
(2017/11/24)
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- Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes
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A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.
- Topchiy, Maxim A.,Dzhevakov, Pavel B.,Rubina, Margarita S.,Morozov, Oleg S.,Asachenko, Andrey F.,Nechaev, Mikhail S.
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supporting information
p. 1908 - 1914
(2016/04/20)
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- Polycarbazole compd., manufacturing method thereof, and use thereof
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PROBLEM TO BE SOLVED: To provide a novel carbazole compound with a high T1, a production method thereof and a use thereof.SOLUTION: A carbazole compound represented by general formula (1) is used for any one or more layer of a light emitting layer, a hole transport layer and a hole injection layer of an organic EL element, where Arand Arindependently represent a 6-40C aryl group or a 3-40C heteroaryl group or the like.
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Paragraph 0075; 0078
(2016/11/14)
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- Catalytic carbon-nitrogen bond-forming cross-coupling using N-trimethylsilylamines
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Carbon-nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C-N coupling to give multiply C-N coupled products in high yields. The novel C-N cross-coupling reaction was successfully applied to C-N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.
- Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki
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p. 1437 - 1446
(2015/11/16)
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- Effects of solvent and base on the palladium-catalyzed amination: PdCl 2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides
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A readily accessible catalytic system, PdCl2(Ph 3P)2/Ph3P, was developed for the selective arylation of primary anilines with aryl bromides. The strong influence of solvents and bases on the catalytic activity was observed. In refluxing o-xylene, triphenylphosphine shows high efficiency for Pd-catalyzed intermolecular amination reactions. By changing the bases, mono- and diarylation of primary amines could be selectively achieved in high yields. Moreover, the catalytic system showed good toleration for the steric hindrance of anilines. A series of N,N,N′,N′-tetraaryl-1,1′-biphenyl-4,4′- diamines, important intermediates of OLED hole transport materials, were synthesized facilely via coupling reactions between 4,4′-diaminobiphenyls and aryl bromides.
- Cai, Liangzhen,Qian, Xuanying,Song, Wenjing,Liu, Taoping,Tao, Xiaochun,Li, Wanfang,Xie, Xiaomin
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p. 4754 - 4759
(2014/06/24)
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- Nickel-catalyzed triarylamine synthesis: Synthetic and mechanistic aspects
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An improved protocol was described for the amination of chloroarenes with diarylamines under NiCl2(PCy3)2 catalysis in the presence of a Grignard reagent as base. This method fully suits bromo-/iodoarene substrates as well, and even is expanded to certain aryl tosylates. A preliminary investigation into the mechanism suggests that this amination reaction might proceed through NiI and NiIII intermediates rather than via the usually expected Ni0-Ni II cycle.
- Li, Xin-Le,Wu, Wei,Fan, Xin-Heng,Yang, Lian-Ming
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supporting information
p. 1232 - 1236
(2014/03/21)
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- Efficient delayed fluorescence via triplet-triplet annihilation for deep-blue electroluminescence
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Four 2-(styryl)triphenylene derivatives (TSs) were synthesized for deep-blue dopant materials. By using a pyrene-containing compound, DMPPP, as the host, the TS-doped devices exhibited significant delayed fluorescence via triplet-triplet annihilation, providing the highest quantum efficiency of 10.2% and a current efficiency of 12.3 cd A-1. the Partner Organisations 2014.
- Chou,Chou,Chen,Su,Liao,Lin,Lin,Yen,Chen,Cheng
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supporting information
p. 6869 - 6871
(2014/06/23)
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- Reactivity of [K3(phen)8][Cu(NPh2) 2]3 - A possible intermediate in the copper(i)-catalyzed N-arylation of N-phenylaniline
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Complex [K3(phen)8][Cu(NPh2) 2]3 (1, phen = phenanthroline) was isolated from the catalytic C-N cross coupling reaction based on the CuI-phen-tBuOK catalytic system. Complex 1 can react with 4-iodotoluene to give 4-methyl-N,N- diphenylaniline (3a) in 50% yield (based on all available NPh2 - ligands of complex 1). In addition, 1 can also work as an effective catalyst for the C-N coupling reactions under the same reaction conditions, indicating that 1 may be an effective intermediate of the catalytic system. In the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), a radical scavenger, the stoichiometric reaction between complex 1 and 4-iodotoluene was significantly quenched to give a low yield of 12%. The results suggest that the radical path dominates in the reaction, with (phen)KNPh2 as the possible radical source. The structures of 1 and (phen)KNPh2 were both determined by single crystal X-ray diffraction studies.
- Tseng, Chia-Kai,Lee, Chi-Rung,Tseng, Mei-Chun,Han, Chien-Chung,Shyu, Shin-Guang
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p. 7020 - 7027
(2014/05/06)
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- Tuning the photophysical, thermal properties and electronic energy levels in the triphenylamine derivatives by benzoylhydrazone architecture
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A novel of triphenylamine derivatives with more extended π-conjugated systems achieved by benzoylhydrazone architecture were synthesized under mild condition with high yields. The dependence of their photophysical, electrochemistry and thermal properties on their chemical structure is discussed. Compared with the N,N-di(4-methylphenyl)aniline, the thermostability of the five triphenylamine-based hydrozones is dramatically promoted. These compounds are stable up to 345 °C according to thermogravimetric analysis. The energy levels of the four compounds were finely tuned by introducing the electron-donating and -withdrawing groups to the triphenylamine core which are supported by the fluorescence spectra and transit fluorescence spectra of the compounds (-H > -CH3 > -Cl > Pyridine > -NO2). Their multiple cyclic voltammetry study and density functional study suggest these materials to be promising hole-transport properties.
- Liu, Lizeng,Meng, Xianfang,Li, Wei,Zhou, Xueqin,Bai, Zhengchen,Liu, Dongzhi,Lv, Yunrong,Li, Rui-Hong
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- Silicon-based CN cross-coupling reaction
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Palladium-catalyzed CN bond-forming cross-coupling reaction of N-trimethylsilylamines with aryl bromides and chlorides is found to proceed in the presence of a fluoride activator in 1,3-dimethyl-2-imidazolidinone (DMI), giving triarylamines in excellent yields. When aryl bromide and bis(silyl)amine were used in this reaction, double CN bondforming products were obtained in high yields. The present reaction was successfully applied to CN bond-forming polymerization.
- Shimizu, Kenta,Minami, Yasunori,Goto, Osamu,Ikehira, Hideyuki,Hiyama, Tamejiro
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supporting information
p. 438 - 440
(2014/04/17)
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- APPLICATION OF TRIPHENYLENE DERIVATIVES IN ORGANIC ELECTROLUMINESCENT DEVICES
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Triphenylene derivatives having a structure of formula (1) are provided. Ar represents an aromatic compound, n is 1 to 3, and each of R and R1 to R13 is a member independently selected from the group consisting of hydrogen, halo, cyano, trifluoromethyl, amino, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C20 cycloalkyl, C3-C20 cycloalkenyl, C1-C20 heterocycloalkyl, C1-C20 heterocycloalkenyl, aryl and heteroaryl. The compound of the present invention may function as a host emitter or dopant in the emitter layer of OLED device. An OLED device is also herein provided.
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- Iron-catalyzed aromatic amination for nonsymmetrical triarylamine synthesis
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Novel iron-catalyzed amination reactions of various aryl bromides have been developed for the synthesis of diaryl- and triarylamines. The key to the success of this protocol is the use of in situ generated magnesium amides in the presence of a lithium halide, which dramatically increases the product yield. The present method is simple and free of precious and expensive metals and ligands, thus providing a facile route to triarylamines, a recurrent core unit in organic electronic materials as well as pharmaceuticals.
- Hatakeyama, Takuji,Imayoshi, Ryuji,Yoshimoto, Yuya,Ghorai, Sujit K.,Jin, Masayoshi,Takaya, Hikaru,Norisuye, Kazuhiro,Sohrin, Yoshiki,Nakamura, Masaharu
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supporting information
p. 20262 - 20265
(2013/02/23)
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- A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction
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The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity.
- Islam,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir
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experimental part
p. 1352 - 1357
(2011/10/12)
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- Light-emitting dyes derived from bifunctional chromophores of diarylamine and oxadiazole: Synthesis, crystal structure, photophysics and electroluminescence
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The synthesis, structural, photophysical, electrochemical and electroluminescent properties of a novel class of bifunctional molecule are reported in which the hole-transporting triarylamine and electron-transporting oxadiazole components were combined. The strongly luminescent compounds displayed good thermal and morphological stability as well as intense fluorescence both in solution and thin film at room temperature. The effects of the introduction of substituents with different electronic properties upon their absorption and emissive characteristics were correlated with theoretical calculations using density functional theory computations. The photophysics and electrochemistry of such systems were compared to those for the corresponding molecule without an oxadiazole ring. The bipolar compounds could be vacuum-sublimed and applied as emissive dopants for the fabrication of electrofluorescent, organic light-emitting devices with relatively simpler device structures, which can emit tunable colors by varying the aryl ring substituents.
- He, Ze,Kan, Chi-Wai,Ho, Cheuk-Lam,Wong, Wai-Yeung,Chui, Chung-Hin,Tong, Ka-Lap,So, Shu-Kong,Lee, Tik-Ho,Leung, Louis M.,Lin, Zhenyang
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experimental part
p. 333 - 343
(2011/06/21)
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- Nickel-catalyzed cross-coupling of diarylamines with haloarenes
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The cross-coupling reaction of diarylamines with aryl bromides/iodides can be effected by the Ni(ii)-(σ-aryl) complex/PPh3/NaH system, and a preliminary investigation was conducted into the mechanism of this reaction.
- Gao, Cai-Yan,Cao, Xingbo,Yang, Lian-Ming
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supporting information; experimental part
p. 3922 - 3925
(2009/12/06)
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- Evaluation of aromatic amination catalyzed by palladium on carbon: A practical synthesis of triarylamines
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A heterogeneous palladium on carbon (Pd/C)-catalyzed coupling between amines and aromatic halides including aromatic chlorides has been achieved using sodium tert-butoxide (NaO-t-Bu) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand in cyclopentyl methyl ether (CPME). The use of potassium tert-butoxide (KO-t-Bu) in place of NaO-t-Bu brought about the benzyne-mediated aromatic amination even without Pd/C and dppf, giving a mixture of regioisomers when 4-substituted bromobenzenes were employed as the substrate. The combination of Pd/C, dppf, NaO-t-Bu could be utilized for the syntheses of a broad range of triarylamines by replacing CPME with mesitylene which can provide a higher reaction temperature. The Pd/C could be quantitatively recovered and reused until at least the fourth cycle without any loss in catalytic activity. The quite low leaching of palladium (1.1%) was demonstrated by an inductively coupled plasma-atomic emission spectrometric analysis.
- Monguchi, Yasunari,Kitamoto, Katsunori,Ikawa, Takashi,Maegawa, Tomohiro,Sajiki, Hironao
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supporting information; experimental part
p. 2767 - 2777
(2009/12/08)
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- Diazabutadiene: a simple and efficient ligand for copper-catalyzed N-arylation of aromatic amines
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Diazabutadienes (DABs) were chosen as ancillary ligands in the Cu-catalyzed C-N coupling reaction for the synthesis of triarylamines. A combination of CuI/DAB (1) [1: N,N′-bis(2,6-diisopropylphenyl)-1,4-diaza-1,3-butadiene] was found to be an efficient catalyst system for N-arylation of diarylamines and anilines with aryl iodides, affording the desired products in good to excellent yields.
- Liu, Yu-Hua,Chen, Chen,Yang, Lian-Ming
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p. 9275 - 9278
(2007/10/03)
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- Arylation of diarylamines catalyzed by Ni(II)-PPh3 system
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(Chemical Equation Presented) The cross-coupling of bromomagnesium diarylamides, generated in situ from diarylamines, with aryl bromides or iodides can be effected with a simple NiCl2(PPh3) 2-PPh3 catalyst system under relatively mild conditions. This coupling reaction is an inexpensive, convenient, and practical method, functioning as an alternative to the corresponding Pd-catalyzed or Cu-mediated process for the synthesis of triarylamines.
- Chen, Chen,Yang, Lian-Ming
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p. 2209 - 2211
(2007/10/03)
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- Bis(aminostyryl)benzene compounds and synthetic intermediates thereof, and process for preparing the compounds and intermediates
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To provide compounds, which are suitable for use as an organic luminescent material capable of developing intense luminescence which is yellow to red, and a process for preparing in general and high efficiency. A bis(aminostyryl)benzene compound of the following general formula [I] is provided wherein R2and R3independently represent an unsubstituted aryl group, and R1and R4independently represent an aryl group, and R5to R8, independently represent a cyano group or the like. A process for the preparation thereof is described wherein a 4-(N,N-diarylamino)benzaldehyde and a diphosphonic acid ester or diphosphonium are subjected to condensation reaction. Intermediates of the bis(aminostyryl)benzene compound are also described.
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- Catalytic Synthesis of Triarylamines
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Condensation along Ullman reaction in the presence of copper catalysts was carried out with para-substituted arylamines and p-iodotoluene to yield the corresponding triarylamines. For preparation of diarylamines was used dehydrogenation of N-cycloalkylanilines and azomethines; diarylamines were obtained through dehydroamination of cycloaliphatic alcohols with anilines.
- Tarasievich,Mikhalevskaya,Kozlov
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p. 1100 - 1102
(2007/10/03)
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- Arylamine processes
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A process for the preparation of triarylamines which comprises the reaction of an aniline and a haloaromatic component in the presence of a ligand copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120° C. to about 150° C.
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- Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. II. N-Phenylation of Diarylamines
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The condensations of 1,4-cyclohexanedione with several diphenylamines were investigated in order to determine the limit of the utility of this reaction for the N-phenylation of aromatic secondary amines. 4-Methoxy-, 4,4'-dimethyl-, and 4,4'-dibromodiphenylamines produced their N-phenylated compounds in fairly good yields, but 4-hydroxy-, 3-methoxy-, and 4,4'-bis(dimethylamino)diphenylamines produced poor yields.Nitro-substituted diphenylamines gave N-phenyl derivatives in low yields along with N-4-hydroxyphenyl derivatives.N,N'-Diphenyl-p-phenylenediamine and N,N'-diphenylbenzidine gave correspondig tetra-N-phenyl diamines in good yields.The condensation of N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-2-pyridylamine, phenothiazine, and carbazole with 1,4-cyclohexanedione were also examined.
- Haga, Kazuo,Iwaya, Katsumasa,Kaneko, Ryohei
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p. 803 - 808
(2007/10/02)
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