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scalable access to functionalized 1,1’- and 1,2-ferrocenyl azides has been realized
in flow. By halogen‒lithium
exchange of ferrocenyl halides and subsequent reaction with tosyl azide, a
variety of functionalized ferrocenyl azides was obtained in high yields. To
allow a scalable preparation of these potentially explosive compounds, an
efficient flow protocol was developed accelerating the reaction time to minutes
and circumventing accumulation of potentially hazardous intermediates.
Switching from homogeneous to triphasic flow amidst process was key for
handling a heterogeneous reaction mixture formed after a heated reactor section.
The corresponding and synthetically versatile ferrocenyl amines were then
prepared by a reliable reduction process.