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Updated: Jul 11, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Phosphine Catalysis of the Fluorination of Unactivated Tertiary Alkyl Chlorides under Mild and Convenient Conditions
Zhuo-Yan Wang1, Dylan J Freas1, Gregory C Fu1
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
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.
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