10228-84-9Relevant academic research and scientific papers
Palladium-catalyzed aerobic oxidative hydroamination of vinylarenes using anilines: A wacker-type amination pathway
Song, Eunsun,Kim, Hun Young,Oh, Kyungsoo
, p. 5264 - 5267 (2017)
A palladium-catalyzed intermolecular hydroamination of vinylarene derivatives using anilines has been developed for the first time under aerobic conditions, where the regioselective formation of N-arylketimines is accomplished. The current aerobic oxidative hydroamination pathway of anilines is distinct from that of palladiumcatalyzed hydroamination reactions that proceed to give sec-arylethylamine and arylethylamine derivatives, identifying a longstanding missing reaction pathway, Wacker-type amination, to N-arylketimines using anilines. The ready availability of both starting materials, vinylarenes and anilines, offers an attractive and facile synthetic route to N-arylketimines in good to excellent yields.
N-heterocyclic carbenes and imidazole-2-thiones as ligands for the gold(I)-catalysed hydroamination of phenylacetylene
Alvarado, Edwin,Badaj, Anna C.,Larocque, Timothy G.,Lavoie, Gino G.
, p. 12112 - 12121 (2012)
Gold(I) complexes of 1-[1-(2,6-dimethylphenylimino)alkyl]-3-(mesityl) imidazol-2-ylidene (CImineR), 1,3-dimesitylimidazol-2-ylidene (IMes) and of the corresponding thione derivatives (SImineR and IMesS) were prepared and structurally
Palladium(II) complexes bearing an indazole-derived N-heterocyclic carbene and phosphine coligands as catalysts for the Sonogashira coupling and the hydroamination of alkynes
Bernhammer, Jan C.,Chong, Ning Xi,Jothibasu, Ramasamy,Zhou, Binbin,Huynh, Han Vinh
, p. 3607 - 3617 (2014)
Indazolin-3-ylidenes (indy) are among the most strongly donating N-heterocyclic carbenes, but the structural diversity of their complexes is still limited. Two dimeric palladium(II) complexes, [PdBr2(indy-5)] 2 (2a) and [PdBr2(indy-6)]2 (2b) (indy-5 = 2,3-dihydro-1H-pyrazolo[1,2-a]indazolin-3-ylidene, indy-6 = 6,7,8,9- tetrahydropyridazino[1,2-a]indazolin-3-ylidene], bearing indazolin-3-ylidene ligands with different sizes of the fused aliphatic ring can be obtained by silver carbene transfer. The reaction of these dimers with pyridine yielded trans-[PdBr2(indy)(pyridine)] complexes (3a,b), while the poorly soluble monophosphine complexes cis-[PdBr2(indy)(PPh3)] (4a,b) were obtained by reaction with triphenylphosphine. Ligand substitution of the latter with silver trifluoroacetate afforded cis-[Pd(O2CCF 3)2(indy)(PPh3)] complexes (5a,b) with improved solubilities, allowing for their detailed characterizations. In the presence of sodium tetrafluoroborate, cationic bis(phosphine) complexes trans-[PdBr(PPh3)2][BF4] (6a,b) could be obtained. Similarly, cis-[PdBr(dppe)][BF4] (7a,b) and cis-[PdBr(dppp)][BF4] (8a,b) were obtained (dppe = bis(diphenylphosphino)ethane; dppp = bis(diphenylphosphino)propane) with the respective chelating diphosphines. A preliminary catalytic study revealed that the complexes incorporating monodentate phosphine ligands are good catalysts for the Sonogashira cross-coupling, while moderate to good yields were achieved with all complexes for the hydroamination of carbon-carbon triple bonds.
Benzimidazolin-2-ylidene complexes of palladium(II) featuring a thioether moiety: Synthesis, characterization, molecular dynamics, and catalytic activities
Bernhammer, Jan C.,Huynh, Han Vinh
, p. 1266 - 1275 (2014)
Six benzimidazolin-2-ylidene palladium(II) complexes with an alkyl-alkyl thioether moiety in the side chain have been synthesized. Due to the hemilabile metal-sulfur bond, the complexes exhibit a marked fluxionality, as evidenced by NMR studies. The thioe
Hydroamination reactions catalyzed by [Au2(μ-Cl)(μ-bis(phosphino)ferrocene)][BArF24]
Wolfarth, Sadie A.,Miner, Natasha E.,Wamser, Nicole E.,Gwinn, Reilly K.,Chan, Benny C.,Nataro, Chip
, (2020)
1,1′-bis(phosphino)ferrocene ligands are commonly employed in a variety of catalytic systems. These ligands are of particular interest as the steric and electronic properties of the phosphorus donor atoms can be altered by changing the substituents of the
Phosphinimino-amino magnesium complexes: Synthesis and catalysis of heteroselective rop of rac -lactide
Xie, Hongyan,Mou, Zehuai,Liu, Bo,Li, Ping,Rong, Weifeng,Li, Shihui,Cui, Dongmei
, p. 722 - 730 (2014)
Alkane elimination reactions of phosphinimino-amine ligands HL 1-8 ((2,6-Me2-C6H3NH)C(Ph)i - CHPPh2(NAr) (Ar = C6H5 (HL1); 2,6-Me2-C6H3/sub
Gold(I) complexes bearing ring-fused benzoxazine-derived triazolylidenes and their use in C–N bond-forming processes
Campos-Dominguez, Emmanuel,Vasquez-Perez, Jose,Rojas-Lima, Susana,Lopez-Ruiz, Heraclio,Mendoza-Espinosa, Daniel
, (2020/12/07)
We report the synthesis and full characterization of a novel series of ring-fused benzoxazine-derived triazolium salts (1a–c) and their corresponding triazolylidene gold(I) complexes (2a–c). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and mass spectroscopy and in the case of triazoliums 1a and 1b by single-crystal X-ray diffraction. The new triazolylidene gold complexes (2a–c) were tested as precatalysts in the hydroamination and hydrohydrazination of terminal alkynes employing aniline derivatives and hydrazine as nitrogen sources, respectively.
Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
Virant, Miha,Mihela?, Mateja,Gazvoda, Martin,Cotman, Andrej E.,Frantar, Anja,Pinter, Balazs,Ko?mrlj, Janez
supporting information, p. 2157 - 2161 (2020/02/13)
The cationic palladium(II) complex 1 of pyridyl-mesoionic carbene ligand catalyzes Markovnikov-selective intermolecular hydroamination between anilines and terminal alkynes into the corresponding imines. The reaction proceeds at room temperature, in the a
HΒ Catalyzed Condensation Reaction Between Aromatic Ketones and Anilines: To Access Ketimines (Imines)
Amrutham, Vasu,Mameda, Naresh,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Gajula, Krishna Sai,Grigor’eva, Nellya Gennadievna,Nama, Narender
, p. 2982 - 2986 (2017/10/09)
Abstract: A simple approach for the formation of imines by condensation of ketones and anilines over heterogeneous catalyst (Hβ zeolite) has been successfully developed. The present catalytic system scope was explored for various aromatic ketones and anil
Large Cu i 8 chalcogenone cubic cages with non-interacting counter ions
Katam, Srinivas,Ganesan, Prabusankar
supporting information, p. 16615 - 16622 (2017/12/15)
Two mega size copper(i) cubic cages, [{Cu(Bptp)1.5}8(PF6-)](PF6-)7 (1) and [{Cu(Bpsp)1.5}8(PF6-)](PF6-)7 (2), supported by imidazole-2-chalcogenone ligands (Bptp = 2,6-bis(1-isopropylimidazole-2-thione)pyridine and Bpsp = 2,6-bis(1-isopropylimidazole-2-selone)pyridine) have been synthesized and characterized. The formation of ionic salts 1 and 2 was confirmed by FT-IR, multinuclear (1H, 13C, 31P and 19F) NMR, UV-vis, TGA, CHN analysis, BET analysis, single crystal X-ray diffraction and powder X-ray diffraction techniques. To the best of our knowledge, these are the first examples of a octanuclear copper(i) cluster in a perfect cubic architecture with a copper-copper distance of 8.413 ? or 8.593 ?. Interestingly, these anion-centered CuI8 cubic arrangements are not supported by cubic centered ions or face centered molecules. The formation of cationic cubic cages was accompanied by the association of twelve ligands (Bptp or Bpsp) with eight trigonal planar [CuSe3] vertices. The cationic charge of cubic cages was satisfied by eight PF6- counter anions, in which one of the PF6- anions occupies the centre of the Cu8 cube without any interaction. The copper(i) cubic cages are found to be highly active catalysts in click chemistry as well as hydroamination reactions. The scope of the catalytic reactions has been investigated with thirty-five different combinations of click reactions and six different combinations of the hydroamination of alkynes.
