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

The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned...

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Veröffentlicht in:Organic letters 2020-10, Vol.22 (19), p.7537-7541
Hauptverfasser: von Keutz, Timo, Cantillo, David, Kappe, C. Oliver
Format: Artikel
Sprache:eng
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Zusammenfassung:The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized 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. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02725