204066-08-0Relevant articles and documents
Microenvironment modulation of cuprous cluster enables inert aryl chlorides activation in single-molecule metallaphotoredox amination
Ji, Wei,Jing, Su,Li, Ai-Min,Qi, Zheng-Hang,Qiu, Wen-Jie,Zha, Guo-Jin,Zhu, Dun-Ru
, p. 313 - 321 (2022/01/03)
Amination of aryl halides is an important tool in organic synthesis and the activation of inert aryl chlorides is particular difficult. We herein report the first study of aromatic microenvironment modulation of cuprous clusters as single-molecule metalla
Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules
Kundu, Anu,Kumar, Vadivel Vinod,Anthony, Savarimuthu Philip
, (2020/11/05)
Carbon encapsulated copper oxide nanoparticles (CuONPs@C) fabricated using copper metal organic frameworks (Cu-MOFs) used as reusable nanocatalysts in Ullmann C[sbnd]N coupling reactions for synthesizing optoelectronic triphenylamine (TPA) and carbazole (CBZ) derivatives. The formation of CuONPs in carbon matrix was confirmed by powder X-ray diffraction (PXRD), X-ray photoelectron spectroscopy (XPS) and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of CuONPs@C was performed with diphenylamine/carbazole with substituted aryl halides in presence of mild K2CO3 base that produced triarylamines with 63–83% yields. Carbazole triarylamines exhibited strong solid state fluorescence (Φf = 14.54–36.32%) with λmax between 370 and 420 nm.
DIALKYL[2-(PYRENYL)PHENYL]PHOSPHINE, AND CATALYST COMPRISING PALLADIUM COMPOUND AND THE SAME
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Paragraph 0044, (2017/08/16)
PROBLEM TO BE SOLVED: To provide a catalyst which comprises a palladium compound and [2-(pyrenyl)phenyl]phosphine. SOLUTION: The invention uses as a catalyst a complex compound which comprises a palladium compound and [2-(pyrenyl)phenyl]phosphine represen
Photochemical Synthesis of Complex Carbazoles: Evaluation of Electronic Effects in Both UV- and Visible-Light Methods in Continuous Flow
Hernandez-Perez, Augusto C.,Caron, Antoine,Collins, Shawn K.
, p. 16673 - 16678 (2015/11/09)
An evaluation of both a visible-light- and UV-light-mediated synthesis of carbazoles from various triarylamines with differing electronic properties under continuous-flow conditions has been conducted. In general, triarylamines bearing electron-rich groups tend to produce higher yields than triarylamines possessing electron-withdrawing groups. The incorporation of nitrogen-based heterocycles, as well as halogen-containing arenes in carbazole skeletons, was well tolerated, and often synthetically useful complementarity was observed between the UV-light and visible-light (photoredox) methods.
An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride
Nakayama, Yuji,Yokoyama, Naota,Nara, Hideki,Kobayashi, Tohru,Fujiwhara, Mitsuhiko
supporting information, p. 2322 - 2330 (2015/07/27)
An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.
PHOSPHORUS COMPOUND AND TRANSITION METAL COMPLEX OF THE SAME
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Paragraph 0066-0069, (2015/11/10)
The present invention provides a compound represented by general formula (1) and a transition metal complex containing the compound as a ligand: wherein R1 to R10, N, P, Y, and Z have the meanings as defined in DESCRIPTION.
Transition-Metal-Free Synthesis of Carbazoles and Indoles by an SNAr-Based "aromatic Metamorphosis" of Thiaarenes
Bhanuchandra,Murakami, Kei,Vasu, Dhananjayan,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 10234 - 10238 (2015/09/01)
Dibenzothiophene dioxides, which are readily prepared through oxidation of the parent dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The "aromatic metamorphosis" of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron-deficient thiaarene dioxides exhibit interesting reactivity, which is not observed for that the corresponding electron-rich azaarenes, a combination of a thiaarene-dioxide-specific reaction with the SNAr-based aromatic metamorphosis allows transition-metal-free construction of difficult-to-prepare carbazoles.
Efficient synthesis of biscarbazoles by palladium-catalyzed twofold C-N coupling and C-H activation reactions
Hung, Tran Quang,Thang, Ngo Ngoc,Hoang, Do Huy,Dang, Tuan Thanh,Villinger, Alexander,Langer, Peter
, p. 2596 - 2605 (2014/04/17)
A new and efficient strategy for the synthesis of 3,9′- and 2,9′-biscarbazoles was developed. Our strategy relies on the cyclization of 1,1′-biphenyl-2,2′-diyl bis(trifluoromethanesulfonate) with 4- or 3-anisidine, transformation of the methoxy to a triflate group and subsequent oxidative Pd-catalyzed cyclization with various anilines. This journal is the Partner Organisations 2014.
Liquid triarylamines: The scope and limitations of piers-rubinsztajn conditions for obtaining triarylamine-siloxane hybrid materials
Kamino, Brett A.,Mills, Bridget,Reali, Christopher,Gretton, Michael J.,Brook, Michael A.,Bender, Timothy P.
experimental part, p. 1663 - 1674 (2012/04/17)
New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and 19F NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.
Palladium-catalyzed intramolecular C-H arylation of arenes using tosylates and mesylates as electrophiles
Nervig, Christine S.,Waller, Peter J.,Kalyani, Dipannita
supporting information, p. 4838 - 4841,4 (2020/09/16)
This paper describes a method for the palladium catalyzed intramolecular C-H arylation using tosylates and mesylates as electrophiles. The transformation is efficient for the synthesis of various heterocyclic motifs including furans, carbazoles, indoles, and lactams. Additionally, a protocol for the one-pot sequential tosylation/arylation of phenol derivatives is presented.
