Phosphine Catalysis of the Fluorination of Unactivated Tertiary Alkyl Chlorides under Mild and Convenient Conditions
Abstract
Due to the significance of organofluorine compounds in disciplines ranging from medicine to agriculture to materials science, the invention of new methods for the creation of carbon–fluorine bonds is an important objective. Among the underdeveloped dimensions in this area are the fluorination of hindered alkyl halides (particularly chlorides) and the discovery of catalysts for such fluorination processes. Herein, we report a mild method for the fluorination of unactivated tertiary alkyl chlorides (and bromides), catalyzed by inexpensive PPh₃. This straightforward process is compatible with a range of hindered electrophiles and a variety of functional groups.
Copyright and License
© 2023 American Chemical Society.
Acknowledgement
This study is dedicated to the memory of Prof. Jeffery A. Byers (Boston College). We thank Dr. Mona Shahgholi (Mass Spectrometry Facility), Dr. Michael K. Takase (X-ray Crystallography Facility) Dr. David G. Vander Velde (NMR Facility), Dr. Scott C. Virgil (Center for Catalysis and Chemical Synthesis), Carlos E. Del Angel Aguilar, Jay P. Barbor, Hyungdo Cho, Dr. Hien Do, Xiaoyu Tong, Dr. Zhaobin Wang, and Dr. Feng Zhong for assistance and for helpful discussions. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences; grant R35-GM145315), the Beckman Institute of the California Institute of Technology, the Gordon and Betty Moore Foundation (grant to the California Institute of Technology), and the Dow Next-Generation Educator Fund (grant to the California Institute of Technology).
Conflict of Interest
The authors declare no competing financial interest.
Data Availability
CCDC 2294879 and 2294881 contain the supplementary crystallographic data for this paper.
Files
| Name | Size | Download all |
|---|---|---|
|
md5:7fef9e554183d337e9c9cec05edbcbd5
|
7.4 MB | Preview Download |
Additional details
- ISSN
- 1520-5126
- PMCID
- PMC10942731
- National Institutes of Health
- R35-GM145315
- Beckman Institute, California Institute of Technology
- Gordon and Betty Moore Foundation
- Dow Next-Generation Educator Fund