23674-14-8Relevant articles and documents
Molecular Conformations of 9,9'-Bianthryl, Di-9-anthrylmethane, and Some Related Twisted Anthracene Derivatives
Becker, Hans-Dieter,Langer, Vratislav,Sieler, Joachim,Becker, Hans-Christian
, p. 1883 - 1887 (1992)
The molecular conformations of 9,9'-bianthryl (1), its 10,10'-diphenyl derivative (2), 9-p-toylanthracene (3), and 9,10-diphenylanthracene (4) have been investigated by X-ray diffraction.The dihedral angle between the two aromatic ring systems in crystall
When Anthracene and Quinone Avoid Cycloaddition: Acid-Catalyzed Redox Neutral Functionalization of Anthracene to Aryl Ethers
Ding, Nan,Ding, Nan,Ding, Nan,Li, Zhi
supporting information, p. 4276 - 4282 (2020/06/04)
Benzoquinone and 9-phenylanthracene barely undergo anticipated cycloaddition under acid catalysis. Instead, 9-anthracenyl aryl ethers are obtained as unexpected products. Mechanistic studies indicate that the reaction likely undergoes an ionic mechanism between protonated anthracene species and nucleophilic oxygen of 1,4-benzoquinone or 1,4-hydroquinone. A variety of 9-anthracenyl aryl ethers are constructed with this method. Produced anthracenyl aryl ethers are potential scaffolds for new fluorescent molecules.
Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study
Han, Bo,Ma, Pengchen,Cong, Xuefeng,Chen, Hui,Zeng, Xiaoming
supporting information, p. 9018 - 9026 (2019/06/13)
Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theoretical mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs.
Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions
Gribanov, Pavel S.,Golenko, Yulia D.,Topchiy, Maxim A.,Minaeva, Lidiya I.,Asachenko, Andrey F.,Nechaev, Mikhail S.
supporting information, p. 120 - 125 (2018/01/17)
Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille cross-coupling, and one-pot, two-step stannylation/Stille cross-coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 [Pd(OAc)2/PCy3] under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes the SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls in a one-pot two-step procedure.
Palladium catalyzed desulfinylative couplings between aryl sulfinates and aryl bromide/iodide for the synthesis of biaryls
Gund, Sitaram Haribhau,Balsane, Kishor Eknath,Nagarkar, Jayashree Milind
, p. 5051 - 5056 (2016/07/25)
We have synthesized biaryls from the coupling reaction between aryl sulfinates and aryl halides using homogeneous palladium catalytic system. The developed method is simple and efficient. These methodologies are particularly useful to prepare symmetrical as well as unsymmetrical biaryls with excellent product yield. The suggested protocol demonstrated a broad substrate scope.
Mixed NHC/Phosphine Ni(II) Complexes: Synthesis and Their Applications as Versatile Catalysts for Selective Cross-Couplings of ArMgX with Aryl Chlorides, Fluorides, and Methyl Ethers
Zhang, Jie,Xu, Jin,Xu, Yanchao,Sun, Hongmei,Shen, Qi,Zhang, Yong
, p. 5792 - 5800 (2016/01/12)
New methods for the preparation of mixed NHC/phosphine Ni(II) complexes have been developed. It was shown that the quaternary ammonium cation in the easily available Ni(II) complexes [NEt4][Ni(PPh3)X3] (X = Cl and Br) can act as a good leaving group in reactions of [NEt4][Ni(PPh3)X3] with the bulky ItBu (ItBu = 1,3-ditertbutylimidazol-2-ylidene) or IPr [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] ligand, resulting in the corresponding mixed NHC/PPh3 Ni(II) complexes Ni(PPh3)(ItBu)X2 (X = Cl, 1; X = Br, 2) or Ni(PPh3)(IPr)Br2 (3) in high yields. The PPh3 ligand in these obtained mixed NHC/PPh3 Ni(II) complexes can be easily substituted by a more electron-donating phosphine ligand, i.e., PCy3, resulting in the corresponding mixed NHC/PCy3 Ni(II) complexes Ni(PCy3)(ItBu)Br2 (4) and Ni(PCy3)(IPr)Br2 (5) in high yields. The crystal structures of these Ni(II) complexes have been characterized, which revealed a trans disposition of the NHC ligand to the phosphine ligand. The catalytic behaviors of them on varying the carbene ligand (ItBu vs IPr) as well as the phosphine ligand (PPh3 vs PCy3) were investigated in the cross-coupling of aryl Grignard reagents with a wide range of electrophiles. In addition to a significant synergic effect on their catalytic activities, high selectivity for the activation and transformation of C-Cl, C-F and C-O bonds was achieved based on the rational structural design. Complex 2 showed the highest catalytic activity for the cross-coupling of aryl chlorides and fluorides with aryl Grignard reagents, but exhibit little activity for the cross-coupling of aryl methyl ethers with aryl Grignard reagents. On contrast, complex 4 showed great potential for the aryl methyl ethers involved cross-coupling reactions, although its reactivity for the activation of the C-X bond is very poor. The difference in catalytic activity between 2 and 4 has been successfully employed to construct oligoarenes by selective cross-coupling reactions.
Side substituent dependence of photophysical properties of 9-arylanthracene-based π-conjugates
Jana, Debabrata,Ghorai, Binay K.
, p. 88 - 89 (2015/01/30)
Three new 9-arylanthracene-based π-conjugated derivatives with different side substituent (methyl, methoxy, and hexyloxy) were synthesized using Heck coupling/ HornerEmmons reaction in good yields (7278%) and their photophysical properties investigated. T
Novel aromatic compounds for organic light-emitting diode and organic light-emitting diode including the same
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Paragraph 0223-0226, (2016/10/09)
The present invention relates to an organic light emitting compound represented by chemical formula A, and to an organic light emitting device comprising the same. In the chemical formula A, a cyclic group A_1 to A_3, R_1 to R_11, L, n, a structural formula Q, and a structural formula Aandprime; are the same as described in the specification.COPYRIGHT KIPO 2016
Suzuki-miyaura cross-coupling under solvent-free conditions
Asachenko, Andrey F.,Sorochkina, Kristina R.,Dzhevakov, Pavel B.,Topchiy, Maxim A.,Nechaev, Mikhail S.
, p. 3553 - 3557 (2014/01/06)
A solvent-free reaction protocol for Suzuki-Miyaura cross-couplings was developed. (Hetero)aryl bromides and chlorides are coupled with pinacol arylboronates in high yields. The reaction is catalyzed by conventional bis(triphenylphosphine)palladium(II) chloride [(PPh3) 2PdCl2] and/or palladium(II) acetate/SPhos [Pd(OAc) 2/SPhos] under air. Copyright
Suzuki-Miyaura cross-coupling of bulky anthracenyl carboxylates by using pincer nickel N-heterocyclic carbene complexes: An efficient protocol to access fluorescent anthracene derivatives
Xu, Mizhi,Li, Xingbao,Sun, Zheming,Tu, Tao
supporting information, p. 11539 - 11541 (2013/12/04)
A series of fluorescent (hetero)-aryl substituted anthracene derivatives were readily accessible from the corresponding bulky anthracen-9-yl carboxylates via Suzuki-Miyaura cross-coupling reactions by using pincer nickel N-heterocyclic carbene complex 1 even at the catalyst loading as low as 0.1 mol% in the presence of catalytic amounts of PCy3.
