Howard, JL, Sagatov, Y, Repusseau, L et al. (2 more authors) (2017) Controlling reactivity through liquid assisted grinding: the curious case of mechanochemical fluorination. Green Chemistry, 19 (12). pp. 2798-2802. ISSN 1463-9262
Abstract
We have identified an example of a mechanochemically milled organic reaction where liquid-assisted grinding controls the selectivity, such a phenomenon has not been reported/observed before. It was found that upon milling dibenzoylmethane with Selectfluor in the absence of any solvent, a 3 : 1 ratio of monofluorinated : difluorinated product was observed. Whereas, addition of 0.125 mL of acetonitrile (∼10% of the total volume of materials present) to the ground reaction mixture afforded 50 : 1 selectivity. Furthermore, this phenomenon is applicable to a small range of diketone substrates thus far explored. Additionally, we have demonstrated that difluorination can be achieved by simply switching from adding acetonitrile to addition of sodium carbonate. Most notable, in the latter case, is the reduced reaction time compared to a conventional solvent approach, 2 hours in the mill and 24 hours in the flask.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Dates: |
|
Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Inorganic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 12 Jun 2018 15:28 |
Last Modified: | 12 Jun 2018 15:28 |
Status: | Published |
Publisher: | Royal Society of Chemistry (RSC) |
Identification Number: | 10.1039/C6GC03139K |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:131883 |