A Practical, Large-Scale Synthesis of Pyrene-2-Carboxylic Acid

Casas‐Solvas, Juan M.; Mooibroek, Tiddo J.; Sandramurthy, Shugantan; Howgego, Joshua; Davis, Anthony P.

doi:10.1055/s-0034-1379026

Cited by 9 publications

(2 citation statements)

References 9 publications

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“…Pyrene and naphthalene were less reactive under the same ball milling conditions and reactions stopped at the stage of formation of product 3 and 15 . One-step preparation of quinone 30 [39], was achieved by melting reactants at 140 °C for 10 min. Under these conditions, a mixture of adducts 3 and 30 (1.5:1 ratio) was obtained.…”

Section: Resultsmentioning

confidence: 99%

Mechanochemical Friedel–Crafts acylations

Đud¹,

Briš²,

Jušinski³

et al. 2019

Beilstein J. Org. Chem.

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Friedel–Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

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Section: Resultsmentioning

confidence: 99%

Mechanochemical Friedel–Crafts acylations

Đud¹,

Briš²,

Jušinski³

et al. 2019

Beilstein J. Org. Chem.

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“…In the context of a critical analysis of the synthesis possibility of 1,3-dibromopyrene, 2-pyrenecarboxylic acid was synthesised via multistep synthetic routes starting from pyrene [ 79 ], followed by bromination in nitrobenzene. Although the decarboxylation reaction was attempted multiple times, and alternative decarboxylation methods were explored by us according to the protocols of described in the literature for the decarboxylation of carboxylic acids of arenes, the desired product was not obtained ( Table 7 ).…”

Section: Introduction Of Brominementioning

confidence: 99%

Bromopyrene Symphony: Synthesis and Characterisation of Isomeric Derivatives at Non-K Region and Nodal Positions for Diverse Functionalisation Strategies

Zych,

Kubis

2024

Molecules

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Pyrene, a renowned aromatic hydrocarbon, continues to captivate researchers due to its versatile properties and potential applications across various scientific domains. Among its derivatives, bromopyrenes stand out for their significance in synthetic chemistry, materials science, and environmental studies. The strategic functionalisation of pyrene at non-K region and nodal positions is crucial for expanding its utility, allowing for diverse functionalisation strategies. Bromo-substituted precursors serve as vital intermediates in synthetic routes; however, the substitution pattern of bromoderivatives significantly impacts their subsequent functionalisation and properties, posing challenges in synthesis and purification. Understanding the distinct electronic structure of pyrene is pivotal, dictating the preferential electrophilic aromatic substitution reactions at specific positions. Despite the wealth of literature, contradictions and complexities persist in synthesising suitably substituted bromopyrenes due to the unpredictable nature of substitution reactions. Building upon historical precedents, this study provides a comprehensive overview of bromine introduction in pyrene derivatives, offering optimised synthesis conditions based on laboratory research. Specifically, the synthesis of mono-, di-, tri-, and tetrabromopyrene isomers at non-K positions (1-, 3-, 6-, 8-) and nodal positions (2-, 7-) is systematically explored. By elucidating efficient synthetic methodologies and reaction conditions, this research contributes to advancing the synthesis and functionalisation strategies of pyrene derivatives, unlocking new possibilities for their utilisation in various fields.

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