1126-78-9Relevant articles and documents
A highly active bifunctional iridium complex with an alcohol/alkoxide- tethered N-heterocyclic carbene for alkylation of amines with alcohols
Bartoszewicz, Agnieszka,Marcos, Rocio,Sahoo, Suman,Inge, A. Ken,Zou, Xiaodong,Martin-Matute, Belen
, p. 14510 - 14519 (2012)
A series of new iridium(III) complexes containing bidentate N-heterocyclic carbenes (NHC) functionalized with an alcohol or ether group (NHC-OR, R=H, Me) were prepared. The complexes catalyzed the alkylation of anilines with alcohols as latent electrophiles. In particular, biscationic IrIII complexes of the type [Cp*(NHC-OH)Ir(MeCN)]2+2[BF4 -] afforded higher-order amine products with very high efficiency; up to >99 % yield using a 1:1 ratio of reactants and 1-2.5 mol % of Ir, in short reaction times (2-16 h) and under base-free conditions. Quantitative yields were also obtained at 50 °C, although longer reaction times (48-60 h) were needed. A large variety of aromatic amines have been alkylated with primary and secondary alcohols. The reactivity of structurally related iridium(III) complexes was also compared to obtain insights into the mechanism and into the structure of possible catalytic intermediates. The IrIII complexes were stable towards oxygen and moisture, and were characterized by NMR, HRMS, single-crystal X-ray diffraction, and elemental analyses. Copyright
Novel CuO nanoparticle catalyzed C - N cross coupling of amines with Lodobenzene
Rout, Laxmidhar,Jammi, Suribabu,Punniyamurthy
, p. 3397 - 3399 (2007)
CuO nanoparticles catalyze the C-N cross coupling of amines with iodobenzene in excellent yields. The reaction is simple and efficient and operates under air with ligand free conditions. The catalyst is recyclable without loss of activity.
Direct N-alkylation of amines with alcohols using AlCl3 as a Lewis acid
Li, Ya-Qiong,Chen, Yun-Bin,Huang, Zhi-Zhen
, p. 1540 - 1544 (2014)
A substitution reaction of amines with alcohols for N-alkylated amines has been developed using inexpensive AlCl3 without any ligand or additive. Either aromatic or aliphatic amines and primary or secondary alcohols perform the AlCl3-mediated reaction smoothly to afford various N-alkylated amines in satisfactory yields.
RUTHENIUM COMPLEX CATALYZED N-HETEROCYCLIZATION OF AMINOARENES TO QUINOLINE DERIVATIVES USING ALLYLIC ALCOHOLS AND ALIPHATIC ALDEHYDES.
Watanabe,Tsuji,Ohsugi,Shida
, p. 2452 - 2457 (1983)
Aminoarenes reacted with 2-propen-1-ol and 2-buten-1-ol at 180 degree C to give quinoline derivatives in fairly good yields in the presence of a catalytic amount of a ruthenium complex. Dichlorotris(triphenylphosphine)-ruthenium was the most effective catalyst. THe aminoarenes with electron-releasing groups favored the formation of the quinolines. The N-heterocyclization also proceeded when aliphatic aldehydes were used in place of the allylic alcohols. The employment of allylic alcohols gave, however, higher yields in several cases. The reaction involves the isomerization of the allylic alcohols to the corresponding aldehydes. The aldehydes reacted with aminoarenes to give Schiff-base dimers which were then cyclized in the presence of the ruthenium complex to the quinolines. As a key intermediate in the reaction, the ortho-metallated species is proposed.
The facet-dependent enhanced catalytic activity of Pd nanocrystals
Kim, Minjune,Kim, Yeonjoon,Hong, Jong Wook,Ahn, Seihwan,Kim, Woo Youn,Han, Sang Woo
, p. 9454 - 9457 (2014)
A systematic study of heterogeneous Buchwald-Hartwig amination using shape-controlled Pd nanocrystals with distinctly different surface facets is presented. This journal is the Partner Organisations 2014.
French,Pritchard
, p. 903,904, 905 (1961)
[Pd(4-R3Si-IPr)(allyl)Cl], a Family of Silyl-Substituted Pd-NHC Complexes: Catalytic Systems for the Buchwald-Hartwig Amination
Fukaya, Norihisa,Mizusaki, Tomoteru,Hatakeyama, Kouhei,Seo, Yuto,Inaba, Yuuya,Matsumoto, Kazuhiro,Lee, Vladimir Ya.,Takagi, Yukio,Kuwabara, Junpei,Kanbara, Takaki,Choe, Yoong-Kee,Choi, Jun-Chul
, p. 375 - 384 (2019)
A family of Pd-IPr complexes (1Pd-6Pd) featuring electropositive and bulky R3Si substituents at the 4-position of the NHC ring was prepared and fully characterized. The catalytic performance of 1Pd (R3Si = SiMe3) and 3Pd (R3Si = Si(allyl)Me2) in the Buchwald-Hartwig amination was excellent, notably outperforming those of other previously reported catalytic systems by requiring shorter reaction times, lower catalyst loadings, and milder reaction conditions. Furthermore, a systematic evaluation of both the electronic and steric influences of the 4-R3Si-IPr ligand on the overall catalytic performance of 1Pd-6Pd revealed that electronic rather than steric factors play a dominant role.
PHENYLATION OF AROMATIC AND ALIPHATIC AMINES BY PHENYLLEAD TRIACETATE USING COPPER CATALYSIS
Barton, Derek H. R.,Yadav-Bhatnagar, Neerja,Finet, Jean-Pierre,Khamsi, Jamal
, p. 3111 - 3114 (1987)
Copper catalysed phenylation of aromatic and aliphatic amines using phenyllead triacetate has been compared with the analogous reactions using five-valent bismuth derivatives.
Functionalized ionic liquids based on imidazolium cation: Synthesis, characterization and catalytic activity for N-alkylation reaction
Demir, Serpil,Damarhan, Yunus,?zdemir, Ismail
, p. 210 - 215 (2015)
The novel functionalized ionic liquids based on imidazolium cation are synthesized and characterized by studying its 1H, 13C, and 31P NMR and elemental analysis. These ionic liquids have been reported as a highly efficient catalyst for N-alkylation reaction of aniline with butyl chloride. The reaction was efficiently performed in ionic liquid as an environmentally benign solvent with good yields without transition metal.
Ruthenium-catalyzed reductive cyclization of nitroarenes with trialkylamines leading to quinolines
Cho, Chan Sik,Kim, Tae Kyung,Kim, Bok Tae,Kim, Tae-Jeong,Shim, Sang Chul
, p. 65 - 68 (2002)
Nitroarenes react with trialkylamines in the presence of a catalytic amount of a ruthenium catalyst together with tin(H) chloride dihydrate at 180 °C in an aqueous medium (toluene-H2O) to afford the corresponding quinoles in moderate to good yields. The catalytic pathways seems to be proceeded via a sequence involving initial reduction of nitroarenes to anilines, alkyl group transfer from alkylamines to anilines to form an imine, dimerization of imine, and heterocyclization.
Le Guilly et al.
, p. C5 (1972)
Development of Quinoline-2,4(1H,3H)-diones as Potent and Selective Ligands of the Cannabinoid Type 2 Receptor
Han, Shuang,Zhang, Fei-Fei,Qian, Hai-Yan,Chen, Li-Li,Pu, Jian-Bin,Xie, Xin,Chen, Jian-Zhong
, p. 5751 - 5769 (2015)
The cannabinoid type 2 receptors (CB2Rs) play crucial roles in inflammatory diseases. There has been considerable interest in developing potent and selective ligands for CB2R. In this study, quinoline-2,4(1H,3H)-dione analogs have been designed, synthesized, and evaluated for their potencies and binding properties toward the cannabinoid type 1 receptor (CB1R) and CB2R. C5- or C8-substituted quinoline-2,4(1H,3H)-diones demonstrate CB2R agonist activity, while the C6- or C7-substituted analogs are antagonists of CB2R. In addition, oral administration of 21 dose-dependently alleviates the clinical symptoms of experimental autoimmune encephalomyelitis in a mouse model of multiple sclerosis and protects the central nervous system from immune damage. Furthermore, the interaction modes predicted by docking simulations and the 3D-QSAR model generated with CoMFA may offer guidance for further design and modification of CB2R modulators.
Catalytic activity of iron(III), aluminum(III cobalt(II), and magnesium(II) chloride crystal hydrates in the condensation of aniline with butyraldehyde
Bulgakov,Kuleshov,Vafin,Dzhemilev
, p. 944 - 945 (2009)
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Efficient ligand-free copper-catalyzed arylation of aliphatic amines
Yong, Fui-Fong,Teo, Yong-Chua
, p. 3068 - 3072 (2010)
An efficient and practical protocol has been developed for the cross-coupling of alkyl amines and aryl iodides under ligand-free copper(I) iodide catalyzed conditions. A variety of alkyl amines undergo the catalytic system to afford the N-arylated products in moderate to good yields (up to 93%).
A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
supporting information, p. 5222 - 5229 (2021/07/29)
Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols
Huang, Ming,Li, Yinwu,Lan, Xiao-Bing,Liu, Jiahao,Zhao, Cunyuan,Liu, Yan,Ke, Zhuofeng
supporting information, p. 3451 - 3461 (2021/05/03)
Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.
Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols
Nasresfahani, Zahra,Kassaee, Mohamad Z.
, (2020/10/30)
A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.
