Slavik, Petr orcid.org/0000-0002-3326-6169, Trowse, Benjamin, O'Brien, Peter Andrew orcid.org/0000-0002-9966-1962 et al. (1 more author) (2023) Organogel delivery vehicles for the stabilization of organolithium reagents. Nature Chemistry. pp. 319-325. ISSN 1755-4349
Abstract
Organolithium reagents are a vital tool in modern organic chemistry, enabling the synthesis of carbon–carbon bonds. However, due to their high reactivity, low temperatures, inert atmospheres and strictly dried solvents are usually necessary for their use. Here we report an encapsulating method for the stabilization of sensitive organolithium reagents—PhLi, n-BuLi and s-BuLi—in a low-cost hexatriacontane (C36H74) organogel. The use of this technology is showcased in nucleophilic addition reactions under ambient conditions, low-temperature bromine–lithium exchange, ortho-lithiation and C–H functionalization. The gel substantially enhances organolithium stability, allows simple storage, handling and delivery, and enables reproducible reagent portioning. The use of gels as easily divided delivery vehicles for hazardous organometallics has the potential to transform this area of synthetic chemistry, making these powerful reactions safer and more accessible to non-specialist researchers, and enabling the more widespread use of these common synthetic methods.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Author(s) 2023 |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EPSRC EP/R51181X/1 |
Depositing User: | Pure (York) |
Date Deposited: | 17 Feb 2023 08:50 |
Last Modified: | 23 Jan 2025 00:31 |
Published Version: | https://doi.org/10.1038/s41557-023-01136-x |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1038/s41557-023-01136-x |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:196516 |
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Filename: s41557_023_01136_x.pdf
Description: Organogel delivery vehicles for the stabilization of organolithium reagents.
Licence: CC-BY 2.5