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

preprint
submitted 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.

History

Email Address of Submitting Author

philipp.heretsch@fu-berlin.de

Institution

Freie Universität Berlin

Country

Germany

ORCID For Submitting Author

0000-0002-9967-3541

Declaration of Conflict of Interest

none

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