Grindstone chemistry: A “green” approach for the synthesis and derivatization of heterocycles

Banerjee, Mainak; Panjikar, Padmini C.; Das, Dharmendra; Iyer, Shruti; Bhosle, Akhil A.; Chatterjee, Amrita

doi:10.1016/j.tet.2022.132753

Cited by 11 publications

(4 citation statements)

References 231 publications

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“…The experimental apparatuses utilized to activate and drive mechanochemical transformations [15] contribute to making mechanochemistry appealing. Easy to use and characterized by straightforward and versatile design (Figure 3), ball mills and extruders can be regarded as the evolution of mortar and pestle, [16] a ubiquitous tool throughout the history of human beings. Crushing, blending, rubbing, and mixing are no longer entrusted to the hands of researchers but to a set of grinding bodies that eventually make powders undergo a series of compression and shear processes.…”

Section: Mechanochemistry Vs Solvent‐based Chemistrymentioning

confidence: 99%

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

et al. 2022

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Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster new "thinking outside the box", but it also has opened new reaction paths, allowing to overcome the weaknesses of traditional chemistry exactly where the use of well-established solution-based methodologies rules out progress. In this Review, the reader is introduced to an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, the study is mainly focused on organic transformations that, although impossible in solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation and expanding the chemical space.This publication is part of a joint Special Collection of Chemistry-Methods and ChemSusChem including invited contributions focusing on "Methods and Applications in Mechanochemistry". Please visit chemsuschem.org/ collections to view all contributions.

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Section: Mechanochemistry Vs Solvent‐based Chemistrymentioning

confidence: 99%

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

et al. 2022

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“…Methodologies for the Pechmann reaction include microwave, sonication, photocatalysis, and mechanochemical approaches. The last one, i.e., mechanochemical activation, is the main current approach in free-solvent synthetic chemistry and relies on the application of mechanical energy produced from grinding or milling processes to achieve chemical transformations [45][46][47][48][49][50][51].…”

Section: Introductionmentioning

confidence: 99%

“…They reported higher yields of the obtained 4methylcoumarin derivatives; however, two equivalents of catalysts (p-TsOH and P2O5) to the starting phenols were used [41][42][43]. It is known that manual grinding, carried out by a person, is a labor-intensive and non-automatic process, which often raises some concerns, including the kinetic parameters of the reaction and the reproducibility [51]. Although the hand-grinding technique is an easy and inexpensive approach, mechanical milling using a mixer mill or planetary mill by grinding balls (ball-milling) is becoming a more promising green tool for the synthesis of organic molecules, including heterocyclic In this context, Pechmann condensation still attracts a lot of attention from synthetic chemists.…”

Section: Introductionmentioning

confidence: 99%

A Simple and Effective Protocol for the Pechmann Reaction to Obtain 4-Methylcoumarin Derivatives Using a High-Speed Mixer Ball Mill Process

Becerra-Anaya,

Merchán Arenas,

Kouznetsov

2023

Chemistry

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We hereby report a simple and efficient method for the preparation of 4-methylcoumarins series, including Coumarin 120 (7-amino-4-methylcoumarin) from phenols (or naphthols) and ethyl acetoacetate in the presence of 3 mol% InCl3. Coumarins were obtained in good yields (52–92%) through Pechmann condensation, under a rapid and environmentally friendly protocol using a high-speed ball mill mixer at room temperature, with short reaction times, under solvent-free conditions.

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“…In recent times, mechanochemistry [ 45 – 46 ], achieved by mechanical grinding or milling, has garnered massive interest among chemists owing to its green attributes like solvent-free, clean, atom economic, and time-efficient, and has been identified by the IUPAC as one of 10 world-changing technologies [ 47 ]. While milling has received more focus, the simpler form of mechanochemistry, Toda et al’s “grindstone chemistry” [ 48 ] has also been proved as a useful technique for various organic transformations [ 49 ]. It is generally carried out by hand-grinding which is not only a labor-intensive process but also raises some concerns on the reaction kinetics, reproducibility, and scalability.…”

Section: Introductionmentioning

confidence: 99%

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

Das

Bhosle

Chatterjee

et al. 2022

Beilstein J. Org. Chem.

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A simple electrical mortar–pestle was used for the development of a green and facile mechanochemical route for the catalyst-free halogenation of phenols and anilines via liquid-assisted grinding using PEG-400 as the grinding auxiliary. A series of mono-, di-, and tri-halogenated phenols and anilines was synthesized in good to excellent yields within 10–15 min in a chemoselective manner by controlling the stoichiometry of N-halosuccinimides (NXS, X = Br, I, and Cl). It was observed that PEG-400 plays a key role in controlling the reactivity of the substrates and to afford better regioselectivity. Almost exclusive para-selectivity was observed for the aromatic substrates with free o- and p-positions for mono- and dihalogenations. As known, the decarboxylation (or desulfonation) was observed in the case of salicylic acids and anthranilic acids (or sulfanilic acids) leading to 2,4,6-trihalogenated products when 3 equiv of NXS was used. Simple instrumentation, metal-free approach, cost-effectiveness, atom economy, short reaction time, and mild reaction conditions are a few noticeable merits of this environmentally sustainable mechanochemical protocol.

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Grindstone chemistry: A “green” approach for the synthesis and derivatization of heterocycles

Cited by 11 publications

References 231 publications

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

A Simple and Effective Protocol for the Pechmann Reaction to Obtain 4-Methylcoumarin Derivatives Using a High-Speed Mixer Ball Mill Process

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

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