- Benzannulation via ruthenium-catalyzed diol-diene [4+2] cycloaddition: One- and two-directional syntheses of fluoranthenes and acenes
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A new benzannulation protocol is described and applied to the synthesis of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol-diene [4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject to aromatization upon dehydration or Nicholas diol deoxydehydration. Employing diol and tetraol reactants, benzannulation can be conducted efficiently in one- and two-directional modes, respectively, as illustrated in the construction of substituted fluoranthenes and acenes.
- Geary, Laina M.,Chen, Te-Yu,Montgomery, T. Patrick,Krische, Michael J.
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supporting information
p. 5920 - 5922
(2014/05/20)
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- Intramolecular aryl-aryl coupling of fluoroarenes through Al 2O3-mediated HF elimination
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A strategy for effective intramolecular aryl-aryl coupling of fluoroarenes through Al2O3-mediated HF elimination is reported. It is demonstrated that the C-F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group allowing very effective C-C bond formation. The solid-state strategy presented in this study opens the possibility for facile syntheses of insoluble extended polycyclic aromatic hydrocarbons.
- Amsharov, K.Yu.,Merz
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experimental part
p. 5445 - 5448
(2012/08/27)
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- Oligoindenopyrenes: A new class of polycyclic aromatics
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(Graph Presented) A new class of polycyclic aromatic hydrocarbons - oligoindenopyrenes - has been synthesized featuring a Pd-catalyzed Suzuki - Heck coupling cascade. The oligoindenopyrenes are robust, highly colored substructures of C70 and have properties that might prove useful in new organic materials or devices. After excitation, the tetraindenopyrene derivative 3d undergoes efficient deactivation (99%) by internal conversion to the ground state. The small fluorescence quantum yield (0.004) is in accordance with the short (0.6 ns) fluorescence decay time.
- Wegner, Hermann A.,Reisch, Helge,Rauch, Karsten,Demeter, Attila,Zachariasse, Klaas A.,De Meijere, Armin,Scott, Lawrence T.
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p. 9080 - 9087
(2007/10/03)
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- A new Suzuki-Heck-type coupling cascade: Indeno[1,2,3]-annelation of polycyclic aromatic hydrocarbons
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Under palladium catalysis, o-bromobenzeneboronic acid can be coupled with 1-bromonaphthalene (6) and with oligocyclic bromoarenes to furnish indeno-annelated polycyclic aromatic hydrocarbons 1-4 and 25 in a single operation in moderate to good yields (27-87%). Alternatively, o-dibromoarenes and 1,2-dibromocycloalkenes can be cross-coupled with 1-naphthaleneboronic acid under the same conditions to yield analogous products (6-87%), and indenocorannulene (19) can be prepared likewise in a single step from pinacol corannuleneboronate (18) (40%).
- Wegner, Hermann A.,Scott, Lawrence T.,De Meijere, Armin
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p. 883 - 887
(2007/10/03)
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- Short Time Pyrolysis, Part 11 A Simple Synthesis of Dibenzopyracylene
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Dibenzochrysene-7,14-dione (1) and benzopentaphene-5,8-dione (2) on vacuum flow pyrolysis successively eliminate two CO's forming 13H-naphthofluoranthene-13-one (3) and finally indenofluoranthene (dibenzopyracylene). - Keywords: Gas-Phase Pyrolysis, Polycyclic Aromatic Hydrocarbons
- Schaden, Gerhard
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