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Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry
preprintsubmitted on 05.12.2019, 09:13 and posted on 13.12.2019, 05:02 by Merlin Kleoff, Johannes Schwan, Lisa Boeser, Bence Hartmayer, Mathias Christmann, Biprajit Sarkar, Philipp Heretsch
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.
Read the published paper
in Organic Letters