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Mechanochemical electrophilic fluorination of liquid beta-ketoesters

Howard, Joseph L., Sagatov, Yerbol and Browne, Duncan L. 2018. Mechanochemical electrophilic fluorination of liquid beta-ketoesters. Tetrahedron 74 (25) , pp. 3118-3123. 10.1016/j.tet.2017.11.066

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4020
Funders: Engineering and Physical Sciences Research Council
Date of First Compliant Deposit: 3 January 2018
Date of Acceptance: 23 November 2017
Last Modified: 29 Jan 2019 21:49
URI: http://orca.cf.ac.uk/id/eprint/107864

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