Are Grignard Reactions in Deep Eutectic Solvents Interface-Driven? Article Swipe
Iva Manasi
,
Marco Bortoli
,
Daniel T. Bowron
,
Mario Campana
,
Oliver S. Hammond
,
Thomas F. Headen
,
Jake Hooton
,
Eva Hevia
,
Michele Cascella
,
Odile Eisenstein
,
Karen J. Edler
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2024-74pzh-v2
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.26434/chemrxiv-2024-74pzh-v2
Organolithium and organomagnesium addition reactions to ketones are important and versatile processes used in synthetic organic chemistry. However, due to the high reactivity of these species, the reactions are usually done under an inert atmosphere at low temperature. Recent work has demonstrated the possibility to carry out these procedures safely on the benchtop, in air at room temperature using deep eutectic solvents (DES) to dissolve the organic substrate. Surprisingly the organometallic reagent, added in an organic solution, is compatible with these unconventional conditions, and instead of undergoing fast decomposition by the DES, better yields and selectivities are observed than when working under standard conditions. Earlier it was posited that the choline chloride component of the DES might chemically activate the ketone substrate making it more amenable to reaction. Here we probe this hypothesis with experiments; liquid diffraction, neutron reflectometry, NMR and interfacial tension measurements for acetophenone in DES and with all-atom molecular dynamics simulations. We show instead that the role of the choline chloride is to reduce the solubility of the ketone, forcing it to accumulate at the air-solvent (or organic solvent/DES) interface. Molecular dynamics simulations for isopropyl magnesium chloride in the same DES/tetrahydrofuran bi-phase system also indicate a preference to localize at the interface. These results suggest that surface accumulation promotes the addition reaction and account for these remarkable experimental conditions. Accumulation of the organic non-protic substrate at the interface could also protect the organometallic species from rapid decomposition by the protons of the DES.
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- Type
- preprint
- Language
- en
- Landing Page
- https://doi.org/10.26434/chemrxiv-2024-74pzh-v2
- https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/674b14bcf9980725cf96f3bd/original/are-grignard-reactions-in-deep-eutectic-solvents-interface-driven.pdf
- OA Status
- gold
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4404931690
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4404931690Canonical identifier for this work in OpenAlex
- DOI
-
https://doi.org/10.26434/chemrxiv-2024-74pzh-v2Digital Object Identifier
- Title
-
Are Grignard Reactions in Deep Eutectic Solvents Interface-Driven?Work title
- Type
-
preprintOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2024Year of publication
- Publication date
-
2024-12-02Full publication date if available
- Authors
-
Iva Manasi, Marco Bortoli, Daniel T. Bowron, Mario Campana, Oliver S. Hammond, Thomas F. Headen, Jake Hooton, Eva Hevia, Michele Cascella, Odile Eisenstein, Karen J. EdlerList of authors in order
- Landing page
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https://doi.org/10.26434/chemrxiv-2024-74pzh-v2Publisher landing page
- PDF URL
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https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/674b14bcf9980725cf96f3bd/original/are-grignard-reactions-in-deep-eutectic-solvents-interface-driven.pdfDirect link to full text PDF
- Open access
-
YesWhether a free full text is available
- OA status
-
goldOpen access status per OpenAlex
- OA URL
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https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/674b14bcf9980725cf96f3bd/original/are-grignard-reactions-in-deep-eutectic-solvents-interface-driven.pdfDirect OA link when available
- Concepts
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Eutectic system, Interface (matter), Grignard reaction, Materials science, Chemical engineering, Chemistry, Metallurgy, Organic chemistry, Alloy, Engineering, Reagent, Adsorption, Gibbs isothermTop concepts (fields/topics) attached by OpenAlex
- Cited by
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0Total citation count in OpenAlex
- Related works (count)
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10Other works algorithmically related by OpenAlex
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