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Controlling reactivity through liquid assisted grinding: the curious case of mechanochemical fluorination

Howard, Joseph L., Sagatov, Yerbol, Repusseau, Laura, Schotten, Christiane and Browne, Duncan L. 2017. Controlling reactivity through liquid assisted grinding: the curious case of mechanochemical fluorination. Green Chemistry 12 , pp. 2798-2802. 10.1039/C6GC03139K

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1463-9262
Date of First Compliant Deposit: 6 January 2017
Date of Acceptance: 8 December 2016
Last Modified: 25 May 2019 22:55
URI: http://orca.cf.ac.uk/id/eprint/97226

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