Catalytic approach to unsymmetrical [7]-helical indenofluorenes: Cyclotrimerization vs. dehydro-Diels-Alder reaction pathways

Caivano, Ilaria; Bingel, Selina; Cı́sařová, Ivana; Nečas, David; Kotora, Martin

doi:10.1016/j.cattod.2021.12.003

Cited by 3 publications

(2 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Lower reaction temperatures, however, led to very slow or now reactions at all. It should be also mentioned that rather low asymmetric induction was observed during our previous attempts to synthesize enantioenriched unsymmetrical [7]helical indenofluorenes by cyclotrimerization of substrates bearing one phenanthrene moiety [40] …”

Section: Resultsmentioning

confidence: 99%

“…As for the formation of 3 , we propose the following DDA reaction pathway [39b] to rationalize the formation of ketone 3 through steps A−F (Scheme 3 ) that is based on our previous observations during preparation of unsymmetrical [7]indenofluorenes bearing the phenanthrene moiety. [40] The first step involves thermally induced radical annulation of two alkyne moieties to form a dienyl diradical I (step A) in which one radical adds to the aromatic ring forming a new diradical II (step B). The ensuing electron transfer will give rise to the zwitterion III .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Cyclotrimerization Approach to Symmetric [9]Helical Indenofluorenes: Diverting Cyclization Pathways

Cadart

Gläsel

Císařová

et al. 2023

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Catalytic cyclotrimerization routes to symmetrical [9]helical indenofluorene were explored by using different transition–metal complexes and thermal conditions. Depending on the reaction conditions, the cyclotrimerizations were accompanied by dehydro‐Diels–Alder reaction giving rise to another type of aromatic compounds. Structures of both symmetrical [9]helical cyclotrimerization product as well as the dehydro‐Diels–Alder product were confirmed by single‐crystal X‐ray diffraction analyses. Limits of enantioselective cyclotrimerization were assessed as well. DFT calculations shed light on the reaction course and the origin of diminished enantioselectivity.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cyclotrimerization Approach to Symmetric [9]Helical Indenofluorenes: Diverting Cyclization Pathways

Cadart

Gläsel

Císařová

et al. 2023

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks

Feriancová,

Kiss,

Cadart

et al. 2024

Applied Organom Chemis

View full text Add to dashboard Cite

Synthetic options for conversion of indeno[2,1‐c]fluorene‐5,8‐diones into larger polyaromatic compounds with extended π‐conjugated systems were explored. The crucial two‐fold transformation of the five‐membered ketone moieties of indeno[2,1‐c]fluorene‐5,8‐diones was based either on a one‐carbon homologation or on a ring‐expansion reaction which eventually enabled syntheses of compounds possessing substituted tribenzo[a,e,l]indeno[1,2,3‐hi]acephenanthrylenes and [5]helicenes scaffolds. The former was prepared by using a reaction sequence based on Ramirez olefination, intramolecular Heck reaction, and intermolecular Suzuki‐Miyaura cross‐coupling, whereas the latter utilized a sequence comprising Büchner−Curtius−Schlotterbeck reaction and intermolecular Suzuki‐Miyaura cross‐coupling. Scholl reaction of selected [5]helicenes yielded planarized polyaromatic compounds with the tribenzo[a,e,l]indeno[1,2,3‐hi]acephenanthrylene scaffold. Where possible, structures of products were confirmed by X‐ray diffraction analyses. Photophysical properties were determined as well.

show abstract

Pd-catalysed C–H bond functionalisation route to 1,2-dihydroferroceno[c]isoquinoline and its annellated derivatives and the reactivity of these compounds

Varmužová,

Císařová,

Schulz

et al. 2025

Dalton Trans.

View full text Add to dashboard Cite

show abstract

Catalytic approach to unsymmetrical [7]-helical indenofluorenes: Cyclotrimerization vs. dehydro-Diels-Alder reaction pathways

Cited by 3 publications

References 39 publications

Cyclotrimerization Approach to Symmetric [9]Helical Indenofluorenes: Diverting Cyclization Pathways

Cyclotrimerization Approach to Symmetric [9]Helical Indenofluorenes: Diverting Cyclization Pathways

Substituted indeno[2,1‐c]fluorene‐5,8‐diones as a platform for synthesis of polyaromatic hydrocarbons possessing extended π‐conjugated systems with butterfly‐like frameworks

Pd-catalysed C–H bond functionalisation route to 1,2-dihydroferroceno[c]isoquinoline and its annellated derivatives and the reactivity of these compounds

Contact Info

Product

Resources

About