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.