Triphenylene Synthesis Essay

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  • Synthesis of Triphenylene-Based Triptycenes via Suzuki–Miyaura Cross-Coupling and Subsequent Scholl Reaction

    The Journal of Organic Chemistry

    Reinhard, Rominger, and Mastalerz

    201580 (18), pp 9342–9348

    Abstract: A two-step method (Suzuki–Miyaura cross-coupling, followed by Scholl oxidation) to triphenylene-based triptycenes is described, rendering a variety of π-extended triptycenes accessible in high yields and without the necessity of column chromatography ...

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  • Controlling the Scholl Reaction

    The Journal of Organic Chemistry

    King, Kroulík, Robertson, Rempala, Hilton, Korinek and Gortari

    200772 (7), pp 2279–2288

    Abstract: Guidelines for the application of the Scholl reaction were developed. Labeling experiments demonstrate that the Scholl reaction fails in small, unsubstituted oligophenylenes (e.g., o-terphenyl) due to oligomerization of the products (e.g., triphenylene). ...

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  • Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of o-Iodobiphenyls or (Z)-β-Halostyrenes with o-Bromobenzyl Alcohols through Two Sequential C–C Bond Formations Catalyzed by a Palladium Complex

    The Journal of Organic Chemistry

    Iwasaki, Araki, Iino, and Nishihara

    201580 (18), pp 9247–9263

    Abstract:o-Bromobenzyl alcohol has been developed as a novel annulating reagent, bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently ...

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  • Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C–H Activation and Double C–C Bond Formation

    Organic Letters

    Pan, Jiang, Zhang, Chen, and Zhang

    201618 (20), pp 5192–5195

    Abstract: A novel and facile approach for the synthesis of triphenylenes has been developed via palladium-catalyzed coupling of 2-iodobiphenyls and iodobenzenes. The reaction involves dual palladium-catalyzed C–H activations and double palladium-catalyzed C–C bond ...

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  • Selective Even-Numbered Bromination of Triptycene Tris(thiadiazoles)

    Organic Letters

    Kohl, Over, Lohr, Vasylyeva, Rominger, and Mastalerz

    201416 (21), pp 5596–5599

    Abstract: An unusual even-numbered bromination of triptycene tristhiadiazole is described, giving selectively dibromo-, tetrabromo-, and hexabromotriptycenes with two bromines each at the same phenyl ring. The new compounds can be used as precursors for extended π-...

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  • An Oxidative Macrobicyclic Ring Opening of a Triptycene to a Highly Functionalized Fluorene Derivative

    The Journal of Organic Chemistry

    Baumgärtner, Rominger, and Mastalerz

    201580 (17), pp 8881–8886

    Abstract: The treatment of hexamethoxytriptycenes with nitric acid leads to an unprecedented oxidative ring opening of the triptycene scaffold, resulting in a new class of fluorene derivatives with a nitroquinone unit. Preliminary investigations of the influence of ...

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  • Chiral Nanographene Propeller Embedding Six Enantiomerically Stable [5]Helicene Units

    Journal of the American Chemical Society

    Berezhnaia, Roy, Vanthuyne, Villa, Naubron, Rodriguez, Coquerel, and Gingras

    2017139 (51), pp 18508–18511

    Abstract: A one-step synthesis of a nanographene propeller with a D3-symmetry was obtained starting from 7,8-dibromo[5]helicene by Yamamoto nickel(0) couplings. It afforded a chiral polyaromatic hydrocarbon (PAH) embedding six enantiomerically stable [5]helicene ...

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  • Synthesis, Structures, and Properties of Hexapole Helicenes: Assembling Six [5]Helicene Substructures into Highly Twisted Aromatic Systems

    Journal of the American Chemical Society

    Hosokawa, Takahashi, Matsushima, Watanabe, Kikkawa, Azumaya, Tsurusaki, and Kamikawa

    2017139 (51), pp 18512–18521

    Abstract: Hexapole helicenes 1, which contain six [5]helicene substructures, were synthesized by Pd-catalyzed [2+2+2]cycloadditions of aryne precursor 6. Among the possible 20 stereoisomers, which include ten pairs of enantiomers, HH-1 was obtained selectively. ...

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  • A Circularly Arranged Sextuple Triptycene Gear Molecule

    Journal of the American Chemical Society

    Ube, Yamada, Ishida, Sato, Shiro, and Shionoya

    2017139 (46), pp 16470–16473

    Abstract: Herein we report the synthesis of a circularly arranged sextuple triptycene gear molecule, hexakis(10-dodecyloxy-9-triptycyl)ethynylbenzene, via the trimerization of the corresponding triyne with a cobalt catalyst. The six triptycene gears are closely ...

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