Details
| Original language | English |
|---|---|
| Pages (from-to) | 902-907 |
| Number of pages | 6 |
| Journal | Organic letters |
| Volume | 22 |
| Issue number | 3 |
| Early online date | 15 Jan 2020 |
| Publication status | Published - 7 Feb 2020 |
| Externally published | Yes |
Abstract
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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Cite this
- Standard
- Harvard
- Apa
- Vancouver
- BibTeX
- RIS
In: Organic letters, Vol. 22, No. 3, 07.02.2020, p. 902-907.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry
AU - Kleoff, Merlin
AU - Schwan, Johannes
AU - Boeser, Lisa
AU - Hartmayer, Bence
AU - Christmann, Mathias
AU - Sarkar, Biprajit
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by Freie Universität Berlin (Forschungskommissionsmittel to P.H.). We are grateful to Dr. K. Gilmore (Max-Planck Institut für Kolloid- und Grenzflächenforschung, Potsdam), Dr. R. Zimmer, T. Siemon, and C. Hoyer for helpful discussions and to C. Groneberg for HPLC support (all Freie Universität Berlin). We acknowledge the assistance of the Core Facility BioSupraMol supported by the DFG.
PY - 2020/2/7
Y1 - 2020/2/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85078673062&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b04450
DO - 10.1021/acs.orglett.9b04450
M3 - Article
VL - 22
SP - 902
EP - 907
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 3
ER -