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Continuous-flow synthesis of fluorine-containing fine chemicals with integrated benchtop NMR analysis

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Abstract

A compact lab plant was designed for the continuous-flow synthesis of fluorine-containing compounds and was combined with an NMR analysis platform based on a benchtop NMR spectrometer. The approach of a unified synthesis and analysis strategy for fine chemicals was applied to three different reactions, all employing fluorine as a chemical probe for online-19F NMR analysis. A high temperature synthesis for the deprotection of a CF2H group was done as well as Ruppert–Prakash reactions for the perfluoroalkylation of benzaldehyde as a model substrate. The C–H arylation of furan with a trifluoromethylated aryldiazonium salt was performed as an example of a photochemically catalyzed reaction. All three reaction classes challenge the synthesis and analysis setup differently according to sample preparation (premagnetization of bubble-free sample) and spectrometer sensitivity (signal to noise ratio, spectral resolution, scan number, substrate concentration and flow rate), but nonetheless prove the successful application of the continuous-flow synthesis of fluorinated fine chemicals with integrated online NMR analysis.

Graphical abstract: Continuous-flow synthesis of fluorine-containing fine chemicals with integrated benchtop NMR analysis

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Publication details

The article was received on 20 Feb 2017, accepted on 14 Mar 2017 and first published on 24 Mar 2017


Article type: Paper
DOI: 10.1039/C7RE00023E
Citation: React. Chem. Eng., 2017, Advance Article
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    Continuous-flow synthesis of fluorine-containing fine chemicals with integrated benchtop NMR analysis

    T. H. Rehm, C. Hofmann, D. Reinhard, H. Kost, P. Löb, M. Besold, K. Welzel, J. Barten, A. Didenko, D. V. Sevenard, B. Lix, A. R. Hillson and S. D. Riegel, React. Chem. Eng., 2017, Advance Article , DOI: 10.1039/C7RE00023E

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