Ferrocene catalysed C–H arylation of arenes and reaction mechanism study using cyclic voltammetry

Dixit, Swati; Siddiqui, Qamar Tabrez; Muneer, M.; Agarwal, Neeraj

doi:10.1016/j.tetlet.2016.08.020

Cited by 21 publications

(13 citation statements)

References 62 publications

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“…To confirm the content of pyrene in Py‐PAEKs, we had to select the 1 H‐NMR resonance of the TMS as a reference and the mol% of attached pyrene group per PAEK repeating unit was calculated by comparing the resonances intensities of −C(CH3)2− in the polymer backbone (at 1.6–1.7 ppm) and the pyrene groups (at 7.9–8.2 ppm). Comparing with 1 H‐NMR spectra of PAEK and Py‐PAEKs, we found that the 1 H‐NMR resonance at 7.9–8.2 ppm belongs to the pyrene group, which is in agreement with other papers . We used Equation to calculate the actual content of pyrene, the results showed that the calculated content of pyrene in polymers were fit for feed ratios.

6 \int normalmethyl/ 9 true \int pyrenyl = X/Y

…”

Section: Resultssupporting

confidence: 87%

A Novel Graphene Nanoplatelets (GNPs) Dispersant: Polyaryletherketones with Pendent Pyrene Groups

Gao

Sun

et al. 2019

Macro Chemistry & Physics

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Polyaryletherketones (PAEKs) with pendant pyrene groups are prepared and used to functionalize and disperse graphene nanoplates (GNPs). A variety of polymers with a range of pyrene contents are studied. A monomer with pyrene and two hydroxyl groups is designed and synthesized through the Suzuki reaction and used to prepare a series of pyrene‐functioned PAEKs (Py‐PAEKs) by copolymerization. Experiments demonstrate that Py‐PAEKs have not only excellent solubility, but also excellent mechanical properties and outstanding heat resistance. In the same treatment condition, the concentration of GNPs that are modified by Py‐PAEK with 40 molar percentage of pyrene (Py‐40) increases 88 times of the concentration of pure GNPs in NMP. In addition, adding 0.5% GNPs, which is functionalized by Py‐40 to PEEK resin, improves the flexural strength of polymer composite nearly 12% and while the tensile strength of these composites improves nearly 10% with a doubling of the strain at break.

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6 \int normalmethyl/ 9 true \int pyrenyl = X/Y

…”

Section: Resultssupporting

confidence: 87%

A Novel Graphene Nanoplatelets (GNPs) Dispersant: Polyaryletherketones with Pendent Pyrene Groups

Gao

Sun

et al. 2019

Macro Chemistry & Physics

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“…An analogous effect was found in the ferrocene-catalyzed C-H arylation of arenes to produce biaryls. 269 This radical reaction gave an excellent yield for diarylation (products 360b) when an excess of diazonium salt was used. Monoarylation (products 360a) was achieved by using 1 equiv.…”

Section: -Chlorination Of Bodipys With Cucl2mentioning

confidence: 96%

“…and a nitrogen molecule (N2). 269 In contrast to Pd-catalyzed C-H arylation (Scheme 79), this was shown to be a mild and fast derivatization strategy for arylating the BODIPY core. Moreover, this functionalization methodology showed a broad scope: electron-deficient, electron-rich and sterically hindered diazonium salts all reacted regioselectively with BODIPYs 22 at its -positions.…”

Section: -Chlorination Of Bodipys With Cucl2mentioning

confidence: 99%

Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

Boens

Verbelen

Ortiz

et al. 2019

Coordination Chemistry Reviews

299

173

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“…However, little is known about the heterocyclization toward these N-bridged annulated BODIPY systems using substituted BODIPYs and the impact of this complex structures to photophysical properties. Arylation of BODIPYs is a commom chemical approach to produce red-shifted derivatives, which are useful as photosensitizers and biological applications [11].…”

Section: Introductionmentioning

confidence: 99%

Impact of The Arylation of N-Bridged Annulated BODIPY Dyes In Photophysical Properties

Mello

Emery

2021

Preprint

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Functionalization of BODIPY dyes is commonly used to modulate photophysical properties. Among the chemical modification of these dyes, ring fusion indifferent faces of dipyrromethene cores is gaining attention in the literature, due to the modulation ofemission/absorption properties and fluorophores with increased bright. N-bridged annulated BODIPYs were recently synthesized and shows intense bright and blu shifted emission. However, few examples of substituted compounds are described and none involving arylation with extention of the p-conjugation. In this manuscript, it is shown an optimized method for the synthesis of N-bridged annulated BODIPYs, including arylated derivatives, and the studies of molecular properties. It is also shown that fluorinated aryl substituted N-bridged annulated BODIPYs show high quantum yields and are red-shifted compared to unsubstituted examples. The work open opportunities for application of the new developed compounds as probes.

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Ferrocene catalysed C–H arylation of arenes and reaction mechanism study using cyclic voltammetry

Cited by 21 publications

References 62 publications

A Novel Graphene Nanoplatelets (GNPs) Dispersant: Polyaryletherketones with Pendent Pyrene Groups

A Novel Graphene Nanoplatelets (GNPs) Dispersant: Polyaryletherketones with Pendent Pyrene Groups

Synthesis of BODIPY dyes through postfunctionalization of the boron dipyrromethene core

Impact of The Arylation of N-Bridged Annulated BODIPY Dyes In Photophysical Properties

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