Mechanosynthesis of sulfonamides <i>via</i> a telescopic, environmentally friendly, and cost-effective process

Cuccu, Federico; Porcheddu, Andrea

doi:10.1039/d3gc01894f

Green Chem.

2024

DOI: 10.1039/d3gc01894f

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Mechanosynthesis of sulfonamides via a telescopic, environmentally friendly, and cost-effective process

Federico Cuccu,

Andrea Porcheddu

Abstract: Herein we demonstrate the solvent-free mechanochemical approach involving a one-pot-double-steps procedure mediated by solid sodium hypochlorite (NaOCl*5H2O) for sulfonamide synthesis. The protocol entails a tandem oxidation-chlorination reaction on disulfides in...

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Cited by 5 publications

References 88 publications

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Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis

Simone,

Pulpito,

Perna

et al. 2024

Chemistry A European J

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A sustainable and scalable protocol for synthesizing variously functionalized sulfonamides, from amines and sulfonyl chlorides, has been developed using environmentally responsible and reusable choline chloride (ChCl)‐based deep eutectic solvents (DESs). In ChCl/glycerol (1:2 mol mol–1) and ChCl/urea (1:2 mol mol–1), these reactions yield up to 97% under aerobic conditions at ambient temperature within 2–12 h. The practicality of the method is exemplified by the sustainable synthesis of an FFA4 agonist and a key building block en route to anti‐Alzheimer drug BMS‐299897. A subtle interplay of electronic effects and the solubility characteristics of the starting materials in the aforementioned DESs seem to be responsible for driving the reaction successfully over the hydrolysis of sulfonyl chlorides. The procedure’s eco‐friendliness is validated by quantitative metrics like the E‐factor and the EcoScale, with products isolated by extraction or filtration after decantation.

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Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis

Simone,

Pulpito,

Perna

et al. 2024

Chemistry A European J

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Mechanochemistry in Organic Synthesis: An Italian Journey through Innovations

Basoccu,

De Luca,

Porcheddu

2024

Eur J Org Chem

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Mechanochemistry, as an enabling technology, harnesses mechanical force to drive chemical reactions, presenting compelling advantages in organic synthesis within the principles of green chemistry. This review explores how its unique advantages and alignment with sustainable practices have been widely developed in different scientific fields in Italy. As a transformative strategy for organic synthesis, mechanochemistry has been portrayed in this review as a valuable synthetic alternative due to the various advantages, such as solvent reduction and new reaction pathways, that its use brings. Nonetheless, the improvements brought about by its use have also been crucial in other fields of chemistry described by Italian scientists. In this whole context, Italian researchers have analysed both already optimised processes and new feasible pathways, paving the way for new avenues previously hampered by all the limitations that belong to in‐solution chemistry.

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Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control

Xiang,

Shou,

et al. 2024

Green Chem.

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Mechanosynthesis of sulfonamides via a telescopic, environmentally friendly, and cost-effective process

Abstract: Herein we demonstrate the solvent-free mechanochemical approach involving a one-pot-double-steps procedure mediated by solid sodium hypochlorite (NaOCl*5H2O) for sulfonamide synthesis. The protocol entails a tandem oxidation-chlorination reaction on disulfides in...

Cited by 5 publications

References 88 publications

Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis

Switchable Deep Eutectic Solvents for Sustainable Sulfonamide Synthesis

Mechanochemistry in Organic Synthesis: An Italian Journey through Innovations

Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control

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