20743-57-1Relevant academic research and scientific papers
Cu(OTf)2-Mediated Cross-Coupling of Nitriles and N-Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products**
Bell, Nicola L.,Xu, Chao,Fyfe, James W. B.,Vantourout, Julien C.,Brals, Jeremy,Chabbra, Sonia,Bode, Bela E.,Cordes, David B.,Slawin, Alexandra M. Z.,McGuire, Thomas M.,Watson, Allan J. B.
supporting information, p. 7935 - 7940 (2021/03/03)
Metal-catalyzed C–N cross-coupling generally forms C?N bonds by reductive elimination from metal complexes bearing covalent C- and N-ligands. We have identified a Cu-mediated C–N cross-coupling that uses a dative N-ligand in the bond-forming event, which, in contrast to conventional methods, generates reactive cationic products. Mechanistic studies suggest the process operates via transmetalation of an aryl organoboron to a CuII complex bearing neutral N-ligands, such as nitriles or N-heterocycles. Subsequent generation of a putative CuIII complex enables the oxidative C–N coupling to take place, delivering nitrilium intermediates and pyridinium products. The reaction is general for a range of N(sp) and N(sp2) precursors and can be applied to drug synthesis and late-stage N-arylation, and the limitations in the methodology are mechanistically evidenced.
Unified Protocol for Cobalt-Catalyzed Oxidative Assembly of Two Aryl Metal Reagents Using Oxygen as an Oxidant
Liao, Lian-Yan,Liu, Kun-Ming,Duan, Xin-Fang
, p. 9856 - 9867 (2015/11/03)
The first cobalt-catalyzed oxidative cross-coupling reaction of two aryl metal reagents is described. An equivalent amount of two aryl Grignard or lithium reagents, after mediation by an equivalent amount of simple ClTi(OEt)3, was facilely assembled under the catalysis of 1 mol % of CoCl2/10 mol % of DMPU using oxygen. The cross-couplings between various aryl metal reagents, especially between two structurally similar aryl Grignard reagents, proceeded smoothly and selectively and, thus, provided a highly general and efficient method for the construction of biaryl compounds.
A soluble copper(I) source and stable salts of volatile ligands for copper-catalyzed C-X couplings
Maligres, Peter E.,Krska, Shane W.,Dormer, Peter G.
supporting information, p. 7646 - 7651 (2012/11/07)
A stable adduct of CuI with Bu4NI, soluble in organic solvents, has been identified as an effective catalyst for copper-catalyzed C-N and C-O couplings. In addition, stable nonhygroscopic salts of some high performance ligands (diamine MsOH salts/CuX and copper(II) diketonates) were shown to be of similar and sometimes greater reactivity compared to the literature reagents for these couplings. Furthermore, these more robust conditions result in more reproducible results.
Iron-catalyzed C-H and C-C bond cleavage: A direct approach to amides from simple hydrocarbons
Qin, Chong,Zhou, Wang,Chen, Feng,Ou, Yang,Jiao, Ning
supporting information; experimental part, p. 12595 - 12599 (2012/01/15)
Something functional: The title reaction proceeds in the presence of azide and water to deliver amides in high yields, and it can be used in a ring-expansion strategy to generate lactams. A mechanism is proposed based on experimental results. This reaction offers a new approach to functionalizing simple and readily available hydrocarbons. DDQ=2,3-dichloro-5,6-dicyano-1,4- benzoquinone. Copyright
AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT USING THE SAME
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Page/Page column 40, (2009/08/16)
An aromatic amine derivative with a specific structure having a carbazole skeleton to which a diarylamino group bonds via a bonding group. An organic electroluminescence device which is composed of one or more organic thin film layers including at least one light emitting layer sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers contains the aromatic amine derivative singly or as its mixture component. Organic electroluminescence devices with enhanced efficiency of light emission and a compound realizing the devices are provided.
AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME
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Page/Page column 29-30, (2008/12/06)
The present invention provides a novel aromatic amine derivative enabling to obtain an organic electroluminescence device which is driven under a low voltage, exhibits small increase in the driving voltage after continuous driving for a long time and has
AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT EMPLOYING THE SAME
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Page/Page column 25, (2008/06/13)
An aromatic amine derivative having a specific structure having m-terphenyl group and an organic electroluminescence device comprising a cathode, an anode and an organic thin film layer which is disposed between the cathode and the anode and comprises at least one layer comprising at least a light emitting layer, wherein at least one layer in the organic thin film layer comprises the aromatic amine derivative singly or as a component of a mixture. The organic electroluminescence device has a long life.
AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME
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Page/Page column 60-61, (2008/06/13)
Disclosed is an organic electroluminescent device wherein an organic thin film which is composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. Since at least one layer of the organic thin film contains a novel aromatic amine derivative, which has an asymmetric structure wherein two different amine units are bonded through a linking group, by itself or as a component of a mixture, molecules are hardly crystallized, thereby improving the production yield of the organic electroluminescent device. This organic electroluminescent device has a long life.
AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME
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Page/Page column 60, (2008/06/13)
Disclosed is a novel aromatic amine derivative having an asymmetric structure. Also disclosed is an organic electroluminescent device wherein an organic thin film composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. Since at least one layer of the organic thin film contains the aromatic amine derivative by itself or as a component of a mixture, molecules are hardly crystallized, thereby improving the production yield of the organic electroluminescent device. This organic electroluminescent device has a long life.
Structures and excited states of extended and folded mono-, di-, and tri-N-arylbenzamides
Lewis, Frederick D.,Long, Timothy M.,Stern, Charlotte L.,Liu, Weizhong
, p. 3254 - 3262 (2007/10/03)
The relationship between molecular structure and electronic properties of 18 N-arylbenzamides has been investigated. The secondary amides adopt extended trans-amide conformations, whereas the tertiary amides adopt folded cis-amide conformations in which the N-aryl group is approximately perpendicular to the benzoyl group. The N-aryl groups of the tertiary di- and triamides occupy the same face of the benzoyl group and display edge-to-face aryl-aryl interactions. The long-wavelength absorption maxima of the secondary amides are red-shifted as the number of N-aryl groups increases, whereas the tertiary amides display are blue-shifted. ZINDO calculations aid in the assignment of the absorption and luminescence spectra. In all cases the lowest energy singlet state is assigned to a forbidden n,B* (carbonyl lone-pair to benzoyl) transition. The structureless fluorescence of the secondary and tertiary amides is assigned to planar and twisted n.B* singlets, respectively. The allowed absorption bands are assigned to A,B* (arene-to-benzoyl) or A,A* (arene-to-arene) transitions which are localized on a single arene, and the structured phosphorescence is assigned to A,A* triplet states.
