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

M. Kleoff, J. Schwan, L. Boeser, B. Hartmayer, M. Christmann, B. Sarkar, P. Heretsch – 2020

A scalable access to functionalized ferrocenyl azides has been realized in flow. By halogen−lithium exchange of ferrocenyl halides and trapping with tosyl azide, a variety of functionalized ferrocenyl azides were obtained in high yields. To allow a scalable preparation of these potentially explosive compounds, a flow protocol was developed accelerating the reaction time to minutes and circumventing accumulation of potentially hazardous intermediates. The corresponding ferrocenyl amines were then prepared by a reliable reduction process.

Title
Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry
Author
M. Kleoff, J. Schwan, L. Boeser, B. Hartmayer, M. Christmann, B. Sarkar, P. Heretsch
Date
2020
Identifier
DOI: 10.1021/acs.orglett.9b04450
Citation
Org. Lett. 2020, 22, 902–907.