Issue 12, 2017

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
14 11月 2016
Accepted
08 12月 2016
First published
14 12月 2016

Green Chem., 2017,19, 2798-2802

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

J. L. Howard, Y. Sagatov, L. Repusseau, C. Schotten and D. L. Browne, Green Chem., 2017, 19, 2798 DOI: 10.1039/C6GC03139K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements