- Synthesis of Acyl Terphenyls and Higher Polyaromatics via Base-Promoted C-H Functionalization of Acetylarenes with Arylacetylenes
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KOtBu/DMSO-promoted C-H functionalization of acetylarenes with arylacetylenes (100°C, 30 min), generating β,γ-ethylenic ketones, triggers upon further heating (100°C, 4 h, with or without acidifying additive) the cascade assembly of acyl terphenyls and higher polyaromatics in good yields.
- Schmidt, Elena Yu.,Ivanova, Elena V.,Tatarinova, Inna V.,Ushakov, Igor A.,Semenova, Nadezhda V.,Vashchenko, Alexander V.,Trofimov, Boris A.
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- A 1, 4 - diphenyl - 2 - benzoyl benzene preparation method
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The invention discloses a method for preparing 1, 4-diphenyl-2-benzophenone shown as a formula (II). The method includes enabling (E)-1, 4-diphenyl-3-butene-1-ketone in inert organic solvents to carry out stirring reaction under the effects of alkaline substances at the temperature of 70-130 DEG C for 2-25 hours; carrying out post-treatment on reaction liquid to obtain the 1, 4-diphenyl-2-benzophenone shown as the formula (II) after reaction is completed. The (E)-1, 4-diphenyl-3-butene-1-ketone is shown as a formula (I). The method has the advantages of mild reaction conditions, convenience in operation, low cost and broad industrial application prospect.
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Paragraph 0018-0019; 0022; 0024; 0026; 0028; 0030; 0032
(2017/08/25)
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- Base-catalyzed cascade dimerization of γ-aryl-β,γ-enones into acylated terphenyls
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4-Aryl-1-(het)arylbut-3-en-1-ones dimerize smoothly in the ButOK/DMSO superbase system at 100?°C for 4 h to afford acylated terphenyls in up to 79% yield. The dimerization is accompanied by elimination of the methylarene molecule.
- Schmidt, Elena Yu.,Tatarinova, Inna V.,Ushakov, Igor A.,Trofimov, Boris A.
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p. 378 - 379
(2016/10/05)
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- High Fluorescence Efficiencies and Large Stokes Shifts of Folded Fluorophores Consisting of a Pair of Alkenyl-Tethered, π-Stacked Oligo-p-phenylenes
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A series of pure hydrocarbon fluorophores containing a pair of π-stacked oligo-p-phenylenes have been synthesized and analyzed by NMR and X-ray crystallography. They show good fluorescence in solutions and enhanced fluorescence in the aggregated state. Large Stokes shifts (up to 214 nm) have been achieved in these folded fluorophores in virtue of intramolecular energy transfer, and balanced structural rigidity and flexibility. These folded fluorophores provide perfect models for understanding the energy and charge transfer process in π-stacked systems.
- He, Bairong,Nie, Han,Chen, Long,Lou, Xiaoding,Hu, Rongrong,Qin, Anjun,Zhao, Zujin,Tang, Ben Zhong
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p. 6174 - 6177
(2016/01/09)
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- Lewis acid-catalyzed [4 + 2] benzannulation between enynal units and enols or enol ethers: Novel synthetic tools for polysubstituted aromatic compounds including indole and benzofuran derivatives
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The reaction of enynals 1, including o-(alkynyl)benzaldehydes, and carbonyl compounds 2, such as aldehydes and ketones, in the presence of a catalytic amount of AuBr3 in 1,4-dioxane at 100 °C gave the functionalized aromatic compounds 3 in high yields. Similarly, the AuBr3-catalyzed reactions of 1 with acetal compounds 5 afforded the corresponding aromatic compounds 3 in good yields. On the other hand, when the reaction was carried out in the presence of a catalytic amount of Cu(NTf2)2 and 1 equiv of H2O in (CH2Cl)2 at 100 °C, the decarbonylated naphthalene products 4 were obtained selectively over 3. Benzofused heteroaromatic compounds, such as indole derivatives 13 and benzofuran derivatives 15, were also synthesized by using the present benzannulation methodology.
- Asao, Naoki,Aikawa, Haruo
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p. 5249 - 5253
(2007/10/03)
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