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

13 December 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

amines
azides
ferrocenes
flow chemistry
organometallics

Supplementary materials

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