Slavik, Petr orcid.org/0000-0002-3326-6169, O'Brien, Peter Andrew orcid.org/0000-0002-9966-1962 and Smith, David Kelham orcid.org/0000-0002-9881-2714 (2022) Organolithium Gels – Simple Easily Divided Delivery Vehicles for Highly Reactive Species. [Preprint]
Abstract
Organolithium reagents are a vital tool in modern organic chemistry allowing the synthesis of new carbon-carbon bonds. However, due to the high reactivity of organolithiums, the use of low temperatures, inert atmospheres and strictly dried solvents are usually necessary. Here, we report a new encapsulating method for the stabilisation of the sensitive organolithium reagents, PhLi and BuLi (n-BuLi), within 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 and CH functionalisation reactions. The gel significantly enhances the stability of these organolithiums, allows simple handling, delivery and storage, and enables reproducible reagent portioning. The use of gels as easily divided delivery vehicles for hazardous organometallic reagents has the potential to revolutionise this area of synthetic chemistry, making these powerful reactions safer and more accessible to non-specialist researchers, enabling the more widespread use of these common synthetic methods.
Metadata
Item Type: | Preprint |
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Authors/Creators: |
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Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 08 Jun 2023 23:17 |
Last Modified: | 20 Mar 2025 00:15 |
Status: | Published online |
Publisher: | ChemRxiv |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:200215 |
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Filename: organolithium_gels_simple_easily_divided_delivery_vehicles_for_highly_reactive_species.pdf
Description: Organolithium Gels – Simple Easily Divided Delivery Vehicles for Highly Reactive Species