Journal
TETRAHEDRON
Volume 74, Issue 25, Pages 3118-3123Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.11.066
Keywords
Mechanochemistry; Fluorination; Liquid assisted grinding; beta-Ketoesters; Ball mill
Categories
Funding
- Cambridge Reactor Design
- Bolashak International Scholarship of the President of the Republic of Kazakhstan
- EPSRC First Grant Scheme [EP/P002951/1]
- School of Chemistry at Cardiff University
- Engineering and Physical Sciences Research Council [EP/P002951/1] Funding Source: researchfish
- EPSRC [EP/P002951/1] Funding Source: UKRI
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An improved substrate scope for the mechanochemical electrophilic fluorination of dicarbonyls is reported. The applicable substrates have now been broadened to include liquid beta-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. (C) 2017 The Authors. Published by Elsevier Ltd.
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