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Mechanochemical electrophilic fluorination of liquid beta-ketoesters

Howard, JL; Sagatov, Y; Browne, DL; (2018) Mechanochemical electrophilic fluorination of liquid beta-ketoesters. Tetrahedron , 74 (25) pp. 3118-3123. 10.1016/j.tet.2017.11.066. Green open access

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Abstract

An improved substrate scope for the mechanochemical electrophilic fluorination of dicarbonyls is reported. The applicable substrates have now been broadened to include liquid β-ketoesters. Key to this capability is the inclusion of a grinding auxiliary (NaCl) to improve mass transfer and prevent pasting or gumming of the reaction mixture. Notably, the use of a small amount of acetonitrile is critical to increasing the rate of reaction, ensuring complete consumption of starting materials during the short reaction times as well as improving the selectivity for the monofluorinated product in the mill.

Type: Article
Title: Mechanochemical electrophilic fluorination of liquid beta-ketoesters
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.tet.2017.11.066
Publisher version: https://doi.org/10.1016/j.tet.2017.11.066
Language: English
Additional information: This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
Keywords: Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, Mechanochemistry, Fluorination, Liquid assisted grinding, beta-Ketoesters, Ball mill, MEDICINAL CHEMISTRY, 1,3-DICARBONYL COMPOUNDS, ORGANIC-REACTIONS, BALL MILL, SOLVENT, SELECTFLUOR, MULTISTEP, SCALE
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10114335
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