Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions

Costa, Rafaela Gomes Martins da; Farias, Francisco R. L.; Back, Davi F.; Limberger, Jones

doi:10.1016/j.tetlet.2018.01.038

Cited by 12 publications

(9 citation statements)

References 28 publications

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“…Especially important among them are chalcones and β‐aryl‐α,β‐unsaturated enones; for example, 4‐aryl‐3‐buten‐2‐ones . The high biological activity of many chalcone derivatives makes them important materials for the fabrication of drugs against cancer or atherosclerosis . They can also be used in the production of fluorescent probes or optical materials .…”

Section: Introductionmentioning

confidence: 99%

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Wirwis

Trzeciak

2019

Applied Organom Chemis

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Two efficient Pd‐catalyzed tandem pathways for the synthesis of 4,4‐diaryl‐2‐butanones and 4,4‐diaryl‐3‐buten‐2‐ones were elaborated. The first step in both procedures was the Heck coupling of methyl vinyl ketone (MVK) and various aryl iodides leading to 4‐aryl‐3‐buten‐2‐one with the yield of up to 92% in 1 hr. The second step performed with the same catalyst and a new portion of aryl iodide in the presence K2CO3 as a base produced 4,4‐diaryl‐3‐buten‐2‐ones in high yield. Reaction selectivity changed completely to saturated 4,4‐diaryl‐2‐butanones, reductive Heck products, when a tertiary amine was used instead of K2CO3. Due to the application of microwave irradiation (MW), the desired products were obtained in high yield in a short time (4 hr), using 0.5 mol% of the Pd (OAc)2 catalyst without additional ligands.

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Section: Introductionmentioning

confidence: 99%

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Wirwis

Trzeciak

2019

Applied Organom Chemis

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“…Recently, we reported a useful methodology to arylate αand β-positions of chalcones via Heck or Suzuki couplings. 17 In order to obtain β-aryl-TPAchalcones, the Heck protocol (Pd(OAc) 2 , P(o-Tol) 3 , K 2 CO 3 , dimethylformamide (DMF)) was applied to the compounds 4b and 4c, with iodobenzene or iodoanisole as coupling partner. In these conditions, the desired β-arylated dyes 5a and 5b were obtained in 48 and 77% yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…These blue shifts can be attributed to the nonplanarity of β-arylated chalcones derivatives, since a considerable torsion angle between the β-aryl groups and the enone conjugated system was observed on previously described β-arylated chalcones. 17 The substitution pattern also affected the extinction coefficient, since hypochromic effects were observed with the D-π-A compound 4d and with the β-aryl derivatives 5a and 5b.…”

Section: Resultsmentioning

confidence: 99%

“…This result can also be attributed to the diminished conjugation caused by the lack of planarity observed in β-arylchalcones. 17 The fluorescence quantum yields of the compounds 4a-c and 9 were determined in cyclohexane using fluorescein, in alkaline aqueous media (Φ f = 0.93), as a comparison standard. Low Φ f values were observed (1-2%), indicating predominant participation of radiationless relaxation for these dyes.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Photophysical and Electrochemical Properties of Novel D-π-D and D-π-A Triphenylamino-Chalcones and β-Arylchalcones

Costa

Farias

Maqueira

et al. 2018

J. Braz. Chem. Soc.

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A series of triphenylamino (TPA)-chalcones and triphenylamino-β-arylchalcones, displaying either D-π-D or D-π-A architecture, were synthesized through aldol condensations and Heck reactions. The chalcone derivatives display intense absorption bands ranging from 389 to 432 nm and molar extinction coefficients of ca. 10 5 L mol-1 cm-1 corresponding to π-π* electronic transitions. The photoluminescence emissions are peaked between 470 and 563 nm with large Stokes shifts (80-131 nm), attributed to charge transfer in the excited state. The dyes present low fluorescence quantum yields, which is attributed to radiationless excited state deactivation related to aryl rings rotation. Spectroscopic and electrochemical methods were used to determine the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels. Both optical and electrochemical properties of the TPA-chalcone derivatives are considerably affected by the substitution pattern of the chalcones aryl rings and also by the β-arylation of the olefin moiety.

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“…[ 1–5 ] Biological activity of chalcones makes them attractive candidates for fabrication of drugs. [ 6–13 ] The wide range of applications of β‐arylated ketones motivates to search for effective methods of their synthesis. Among them, Heck cross‐coupling represents a direct synthetic strategy, [ 14–17 ] an alternative to the Friedel–Crafts alkylation of aromatic substrates.…”

Section: Introductionmentioning

confidence: 99%

The Heck synthesis of β‐arylated ketones catalyzed by palladium immobilized on functional polysiloxane microspheres

Wirwis

Mizerska

Cypryk

et al. 2020

Applied Organom Chemis

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Palladium catalysts, obtained by the impregnation of Pd(OAc)2 on aminopropyl‐ or pyridine‐functionalized polysiloxane microspheres, were used in the Heck reaction of iodobenzene with 3‐buten‐2‐one and 3‐buten‐2‐ol at 120°C using an oil bath or microwave heating. The synthesis of 4‐phenyl‐3‐buten‐2‐one was one‐step arylation of ketone while 4‐phenyl‐2‐butanone was formed in two‐step arylation–isomerization sequential transformation of alcohol. A very low palladium loading, 0.05 mol%, was sufficient to obtain a yield of ketones higher than 90%. In recycling experiments, an effect of the functional group present in polysiloxane was observed and much better results were obtained for the aminopropyl‐modified polymer. The catalyst was easily retrieved and reused in eight consecutive runs in the reaction of 3‐buten‐2‐one, while with 3‐buten‐2‐ol 11 subsequent cycles were performed with practically the same yield.

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Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions

Cited by 12 publications

References 28 publications

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Synthesis, Photophysical and Electrochemical Properties of Novel D-π-D and D-π-A Triphenylamino-Chalcones and β-Arylchalcones

The Heck synthesis of β‐arylated ketones catalyzed by palladium immobilized on functional polysiloxane microspheres

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