Preparation of polyfunctional diorgano-magnesium and – zinc reagents using in situ trapping halogen-lithium exchange of highly functionalized (hetero)aryl halides in continuous flow

Marthe Ketels, Maximilian Andreas Ganiek, Niels Weidmann, Paul Knochel

• LMU München, Department of Chemistry, München, Germany

We report a halogen-lithium exchange performed in the presence of various metal salts (ZnCl2, MgCl2·LiCl) on a broad range of sensitive bromo- or iodo-(hetero)arenes using BuLi or PhLi as exchange reagent and a commercially available continuous flow setup. The resulting diarylmagnesium or diarylzinc species were trapped with various electrophiles resulting in the formation of polyfunctional (hetero)arenes in high yields. This methodology enabled the functionalization of (hetero)arenes containing highly sensitive groups such as an isothiocyanate, nitro, azide or ester. A straightforward scale-up was possible without further optimization.

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