Organic Chemistry

Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry


A 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.


Thumbnail image of Scalable_Synthesis_of_Functionalized_Ferrocenyl_Azides_and_Amines_Enabled_by_Flow_Chemistry_Heretsch.pdf
download asset Scalable_Synthesis_of_Functionalized_Ferrocenyl_Azides_and_Amines_Enabled_by_Flow_Chemistry_Heretsch.pdf 0.77 MB [opens in a new tab]

Supplementary material

Thumbnail image of SI_Heretsch.pdf
download asset SI_Heretsch.pdf 6 MB [opens in a new tab]
SI Heretsch
Thumbnail image of TOC.jpg
download asset TOC.jpg 0.08 MB [opens in a new tab]