Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates

Timo von Keutz, David Cantillo* and C. Oliver Kappe*

*Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria, Email: david.cantillouni-graz.at, oliver.kappeuni-graz.at

T. von Keutz, D. Cantillo, C. O. Kappe, Org. Lett., 2020, 22, 7537-7541.

DOI: 10.1021/acs.orglett.0c02725

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Abstract

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and a subsequent reaction with aldehydes and ketones provides chlorohydrins and epoxides in good yields within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench.

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Key Words

1,2-addition, chlorohydrins, epoxides, flow chemistry

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ID: J54-Y2020