Reversible Friedel–Crafts acyl rearrangements of planar polycyclic aromatic ketones: dibenzofluorenones

Mala’bi, Tahani; Pogodin, Sergey; Cohen, Shmuel; Agranat, Israel

doi:10.1039/c3ra43483d

Cited by 14 publications

(6 citation statements)

References 39 publications

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“…Furthermore, the product 5fb is more stable than 5fa by 33.7 kJ/mol. Thus, the experimentally observed regioselectivities can be explained in terms of activation barrier differences and product stability: the equivalent reaction profiles observed from 3i accounts for the 5ia/5ib 1:1 ratio and the 5ca/5cb 4:1 ratio results from the higher stability of the former . Finally, 5fa was not observed because of the very unfavourable energetic profile required for its formation compare to 5fb .…”

Section: Resultsmentioning

confidence: 97%

Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

et al. 2019

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The development of an oriented arylation process dedicated to the naphthalene core is presented. Our approach is based on dual role of N‐tosyl carboxamides acting jointly as a directing group in a first C–H arylation step and as a “CO” or “CO–NH” fragment precursor in a further construction step of naphthalene‐based fluorenone or phenanthridinone derivatives. The presence of the directing group in position 1 and 2 of the naphthalene platform allowed selective arylations in position 2 and 3 respectively. Our study represents a first synthetic and general entry of C–H arylation at naphthalene platforms towards the preparation of extended fluorenones as well as benzo‐fused phenanthridinones. Further, the C–H arylation and cyclisation sequence represents a useful way to the preparation of novel extended tetra‐ and pentacyclic fluorenones bearing both electron donating as well as electron withdrawing groups in various substitution patterns. Additionally, both the regioselectivity and the reaction paths of the cyclization leading to the fluorenone architectures was studied by DFT calculations which fully complement experimental observations.

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Section: Resultsmentioning

confidence: 97%

Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

et al. 2019

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“…Among the reactions studied, those related to Friedel-Crafts alkenylation and alkylation showed an interesting dynamic behavior in C-C bond formation and cleavage. Dynamic covalent chemistry is intensively used in various research fields but the Friedel-Crafts alkylation, which is known as "faithfully" reversible compared to acylation, 34 has been virtually ignored so far in this domain. These findings have stimulated further research in our group on this aspect.…”

Section: Discussionmentioning

confidence: 99%

Catalytic applications of [IPr·GaX₂][SbF₆] and related species

et al. 2016

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“…Moreover, we tested the possible reversible Friedel–Crafts acyl rearrangement of 3 d′ to 3 d as observed for planar aromatic ketone . No such rearrangement was observed when 3 d′ was mixed with 20 or even 50 equivalents of TfOH in dichloroethane and heated at 90 °C.…”

Section: Figurementioning

confidence: 99%

Novel Fluorophores based on Regioselective Intramolecular Friedel–Crafts Acylation of the Pyrene Ring Using Triflic Acid

Jousselin‐Oba

Sbargoud

Vaccaro

et al. 2017

Chemistry A European J

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The extension of the pyrene ring from dimethyl 2,2'-(pyrene-1,6-diyl)dibenzoate derivatives by an intramolecular Friedel-Crafts acylation can be realized in an efficient and regioselective manner using triflic acid as proton source. Naphtho-tetracenone derivatives are obtained in high yields at room temperature while Bis-tetracene-diones are prepared upon heating. Both products display interesting fluorescence properties in the visible range with quantum yields varying from 50 to 60 %.

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Reversible Friedel–Crafts acyl rearrangements of planar polycyclic aromatic ketones: dibenzofluorenones

Cited by 14 publications

References 39 publications

Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

Catalytic applications of [IPr·GaX₂][SbF₆] and related species

Novel Fluorophores based on Regioselective Intramolecular Friedel–Crafts Acylation of the Pyrene Ring Using Triflic Acid

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Reversible Friedel–Crafts acyl rearrangements of planar polycyclic aromatic ketones: dibenzofluorenones

Cited by 14 publications

References 39 publications

Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

Site‐Selective Arylation of Naphthalenes: a Key Entry towards Extended Fluorenones and Phenanthridinones

Catalytic applications of [IPr·GaX2][SbF6] and related species

Novel Fluorophores based on Regioselective Intramolecular Friedel–Crafts Acylation of the Pyrene Ring Using Triflic Acid

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Product

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Catalytic applications of [IPr·GaX₂][SbF₆] and related species