58328-31-7Relevant articles and documents
Method for synthesizing 4, 4'-bis (9H-carbazole-9-yl) biphenyl compound in one step
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Paragraph 0022-0028, (2021/02/13)
The invention relates to a method for one-step synthesis of a 4, 4 '-bis (9H-carbazole- 9-yl) biphenyl compound, which comprises the following steps: adding a carbazole compound, a 1, 4-diiodobenzenecompound, organic alkali, a copper salt catalyst, a silver salt oxidant, a phase transfer catalyst and an organic solvent into a reactor, reacting at 120-140 DEG C for more than 12 hours in an air atmosphere, cooling after completion of the reaction, performing organic solvent rotary evaporation, extracting, washing, drying, filtering, performing organic solvent rotary evaporation, and carrying out column chromatography separation to obtain the 4, 4 '-bis (9H-carbazole -9-yl) biphenyl compound. The method provided by the invention realizes one-step synthesis of the product, and has the advantages of high product yield and low preparation cost.
Efficient Copper-Catalysed Synthesis of Carbazoles by Double N -Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air
Do, Ha Nam,Quan, Nguyen Minh,Van Phuc, Ban,Van Tinh, Dinh,Tien, Nguyen Quyet,Nga, Truong Thi Thanh,Nguyen, Van Tuyen,Hung, Tran Quang,Dang, Tuan Thanh,Langer, Peter
supporting information, p. 611 - 615 (2021/01/21)
An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C-N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.
Preparation method of 4,4'-dicarbazolyl biphenyl
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Paragraph 0005; 0016-0022, (2020/05/02)
The invention provides a preparation method of 4,4'-dicarbazolyl biphenyl. 4,4'-dichloro biphenyl and carbazole are effectively coupled to generate 4,4'-dicarbazolyl biphenyl under the action of a 2,6-bis(2,4,6-triisopropylphenyl) phenyl-dicyclohexylphosphine coordinated palladium catalyst and an organic magnesium reagent. The method is characterized in that 2,6-bis (2,4,6-triisopropylphenyl) phenyl-dicyclohexylphosphine is used as a supporting ligand of the palladium catalyst.
Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions
Ageshina, Alexandra A.,Sterligov, Grigorii K.,Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Chesnokov, Gleb A.,Gribanov, Pavel S.,Nechaev, Mikhail S.,Asachenko, Andrey F.,Bermeshev, Maxim V.,Melnikova, Elizaveta K.
, p. 3447 - 3452 (2019/04/30)
A series of novel (NHC)PdCl2-PR3 complexes were synthesized and fully characterized by 1H, 13C, 31P NMR and FT-IR spectroscopy. These complexes showed high catalytic activity toward solvent-free Buchwald-Hartwig amination. Both primary and secondary amines were efficiently utilized under the same reaction conditions. The solvent-free synthesis of valuable N-aryl carbazoles and similar N-heterocyclic systems was described.
Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
, p. 5578 - 5582 (2018/09/25)
A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
A unified strategy for silver-, base-, and oxidant-free direct arylation of C-H bonds
Sahoo, Manoj K.,Midya, Siba P.,Landge, Vinod G.,Balaraman, Ekambaram
supporting information, p. 2111 - 2117 (2017/07/24)
Here, we report a dual catalytic approach for room temperature direct arylation of C-H bonds with aryldiazonium salts as a simple aryl group donor, also working as an internal oxidant via C-N2 bond cleavage. This unified strategy has been achieved by the synergistic combination of visible-light metal-free photoredox and palladium catalysis under silver-, base- and/or additive-free conditions. The broad substrate scope, functional group tolerance, excellent regioselectivity and redox-neutral conditions of this process make it attractive for the effective synthesis of a wide range of important N-heterocyclic commodities such as dibenzo[b,d]azepine, carbazole and phenanthridine.
Synthesis, characterization, and systematic structure–property investigation of a series of carbazole–thiophene derivatives
Damit,Nordin,Ariffin,Sulaiman
, p. 1800 - 1812 (2017/09/25)
A series of carbazole–thiophene oligomers linked at the 3,6-positions of the carbazole fragment of 4,4′-bis(carbazol-9-yl)biphenyl (CBP) and 4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl (CDBP) with systematically elongated molecular lengths were synthesized via the Suzuki–Miyaura and Ullmann coupling reactions. Their electronic properties were studied by UV-Vis, cyclic voltammetry, and theoretical calculations. The coupling of CBP and CDBP with thiophene and bi- and terthiophene residues stabilized the HOMO and LUMO energy levels. The absorption and emission spectra exhibited a gradual red shift. The compounds with oligothiophene units had greatly decreased band gaps compared with CBP and CDBP. Therefore, these units may be introduced into the backbone of π-conjugated small molecules to develop new materials with low band gaps that may have potential applications in optoelectronics.
Synthesis of Novel Derivatives of Carbazole-Thiophene, Their Electronic Properties, and Computational Studies
Damit,Nordin,Ariffin,Sulaiman
, (2016/06/09)
A series of carbazole-thiophene dimers, P1-P9, were synthesized using Suzuki-Miyaura and Ullmann coupling reactions. In P1-P9, carbazole-thiophenes were linked at the N-9 position for different core groups via biphenyl, dimethylbiphenyl, and phenyl. Electronic properties were evaluated by UV-Vis, cyclic voltammogram, and theoretical calculations. Particularly, the effects of conjugation connectivity on photophysical and electrochemical properties, as well as the correlation between carbazole-thiophene and the core, were studied. Carbazole connecting with thiophenes at the 3,6-positions and the phenyl group as a core group leads to increased stabilization of HOMO and LUMO energy levels where the bandgap (Δ E) is significantly reduced.
Oxidative Dimerization of Triarylamines Promoted by WCl6, Including the Solid State Isolation and the Crystallographic Characterization of a Triphenylammonium Salt
Bortoluzzi, Marco,Marchetti, Fabio,Pampaloni, Guido,Pinzino, Calogero,Zacchini, Stefano
, p. 887 - 893 (2016/02/03)
The triphenylammonium salt [NHPh3][WCl6], 1, and the product of the C-C dimerization of triphenylamine, Ph2N(C6H4)2NPh2, 2, were afforded from the reaction between WCl6 and NPh3 in CH2Cl2. Compound 2 was isolated in 43% yield upon hydrolysis of the reaction mixture. The X-ray structure of 1 provides the first crystallographic characterization of the triphenylammonium ion. Combined EPR and DFT studies gave insight into the reaction mechanism, and allowed the identification of WCl5···[Cl(C6H4)NPh2] as a presumable key intermediate. The reactions of WCl6 with 4-bromotriphenylamine, 4,4′-dimethyltriphenylamine, 9-phenylcarbazole, followed by hydrolytic treatment, led to the dimerization products 3-6, in admixture with variable amounts of the parent amines. N,N,N′,N′-tetrakis(4-bromophenyl)-[1,1′-biphenyl]-4,4′-diamine, 3, was isolated in 60% yield from the reaction of WCl6 with 4,4′-dibromotriphenylamine.
Synthesis of substituted 4,4′-dihalobiphenyls and their use for the preparation of isomeric bis(carbazolyl)biphenyls
Kovalev,Pavlyuk,Zaripov,Zyryanov,Kopchuk,Rusinov,Chupakhin
, p. 1978 - 1981 (2016/05/11)
Model compounds of some polychlorobiphenyl congeners, viz., 4,4′-dihalobiphenyls, were synthesized. These compounds can be successfully utilized by a chemical method for the in situ generation of arynes followed by the reaction with carbazole in order to prepare appropriate bis(carbazolyl)biphenyls as components for molecular electronics and OLED devices.
