Ferrocene‐Decorated Phenol Derivatives by Trapping <i>ortho</i>‐Quinone Methide Intermediates with Ferrocene

González‐Pelayo, Silvia; López, Enol; Borge, Javier; de‐los‐Santos‐Álvarez, Noemí; López, Luís A.

doi:10.1002/ejoc.201800396

Cited by 6 publications

(3 citation statements)

References 79 publications

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“…The authors have cited additional references within the Supporting Information (Ref. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40]).…”

Section: Supporting Informationmentioning

confidence: 99%

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Natarajan,

Kanchithalaivan,

Chatterjee

et al. 2024

Asian J Org Chem

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The first chemoselective C4‐benzylation of 5‐aminopyrazoles, utilizing a 3 mol% squaric acid catalyst, is disclosed. In this process, ortho‐quinone methides are efficiently generated from 2‐hydroxybenzyl alcohols in water under mild conditions. This method successfully delivers a wide range of C4‐benzylated 5‐aminopyrazoles, achieving moderate to excellent yields while demonstrating high chemoselectivity, which is further confirmed by mechanistic studies. Notably, the protocol uses water as an eco‐friendly solvent, requires a low organocatalyst loading, and eliminates the need for column chromatography.

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“…The authors have cited additional references within the Supporting Information (Ref. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40]).…”

Section: Supporting Informationmentioning

confidence: 99%

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Natarajan,

Kanchithalaivan,

Chatterjee

et al. 2024

Asian J Org Chem

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“…Regarding the reaction mechanism, both strategies may follow a Friedel-Crafts reaction. However, in the case of Strategy A, polymerization via ortho-quinone methide is also possible, as described by S. Gonzales-Pelayo et al [45]. In contrast, Strategy B can only follow the retro-Friedel-Crafts reaction.…”

Section: Differences In Porosity and Proposed Mechanismmentioning

confidence: 99%

Ferrocene-Based Porous Organic Polymer (FPOP): Synthesis, Characterization and an Electrochemical Study

et al. 2022

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Ferrocene-based porous organic polymers (FPOPs) were prepared from phenol-formaldehyde polymer (Bakelite) and phenol as starting materials; and two possible mechanisms for polymerization were discussed. Solid-state 13C CP-MAS NMR, FTIR, powder XRD, elemental analysis and ICP (Fe, Na, B) were performed to characterize the prepared materials. The two synthetic approaches produced polymers with different pore sizes: the FPOP synthesized through Bakelite presented a higher surface area (52 m2 g−1) when compared to the one obtained by the bottom-up polymerization from phenol (only 5 m2 g−1). Thermogravimetric analysis confirmed the thermal stability of the material, which decomposed at 350 °C. Furthermore, cyclic voltammetry (CV) of the new FPOP on modified electrodes, in ACN and 0.1 M TBAP as an electrolyte, showed fully reversible electron transfer, which is similar to that observed for the ferrocene probe dissolved in the same electrolyte. As a proof-of-concept for an electrochromic device, this novel material was also tested, with a color change detected between yellow/brownish coloration (reduced form) and green/blue coloration (oxidized form). The new hybrid FPOP seems very promising for material science, energy storage and electrochromic applications, as well as for plastic degradation.

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“…In connection with our studies on C–H bond functionalization of ferrocene based on the trapping of highly electrophilic species [ 27 , 28 , 29 ], we have recently described the trapping of ortho -quinone methide intermediates with ferrocene [ 30 ]. Interestingly, some of the ferrocene-containing monophenol derivatives available by this methodology ( Figure 1 c) display remarkable cytotoxic activity against various cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates

et al. 2018

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The reaction of para-hydroxybenzyl alcohols with ferrocene in the presence of a catalytic amount of InCl3 provided ferrocenyl phenol derivatives, an interesting class of organometallic compounds with potential applications in medicinal chemistry. This transformation exhibited a reasonable substrate scope delivering the desired products in synthetically useful yields. Evidence of involvement of a para-quinone methide intermediate in this coupling process was also provided. Preliminary biological evaluation demonstrated that some of the ferrocene derivatives available by this methodology exhibit significant cytotoxicity against several cancer cell lines with IC50 values within the range of 1.07–4.89 μM.

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Ferrocene‐Decorated Phenol Derivatives by Trapping ortho‐Quinone Methide Intermediates with Ferrocene

Cited by 6 publications

References 79 publications

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Organocatalytic Chemoselective C4‐Benzylation of 5‐Aminopyrazoles

Ferrocene-Based Porous Organic Polymer (FPOP): Synthesis, Characterization and an Electrochemical Study

Trapping para-Quinone Methide Intermediates with Ferrocene: Synthesis and Preliminary Biological Evaluation of New Phenol-Ferrocene Conjugates

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