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US 11,779,665 B2Granted
Electrochemical flash fluorination and radiofluorination
AssigneeThe Regents of the University of California
InventorsSaman Sadeghi, Mehrdad Balandeh
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Abstract
Provided herein are methods of fluorinating organic compounds. The electrochemical fluorination and radiofluorination of organic molecules using the cation pool technique is described, where the 18F and/or 19F-fluorine ions are added after the process of electrochemical oxidation, i.e., after formation of a carbocationic organic compound (i.e., a compound having a carbon atom with a positive charge).
Claims11
A method of producing an 18F fluorinated organic compound, the method comprising the steps of:
- (i) performing electrochemical oxidation on a plurality of organic compounds, thereby forming a plurality of carbocations;
- and
- (ii) subsequently adding a plurality of fluorinated nucleophiles to the plurality of carbocations, wherein the plurality of fluorinated nucleophiles comprises 18F-fluorinated nucleophiles and 19F-fluorinated nucleophiles, and wherein the plurality of carbocations is in molar excess relative to the plurality of fluorinated nucleophiles, thereby forming the 18F fluorinated organic compound;
- wherein performing electrochemical oxidation comprises performing electrochemical oxidation in a liquid medium which comprises a mixture comprising:
- (a) the plurality of organic compounds and an organic solvent;
- (b) the plurality of organic compounds, an organic solvent, and an acid;
- (c) the plurality of organic compounds, an organic solvent, and a base;
- (d) the plurality of organic compounds, an acid, and a base;
- or
- (e) the plurality of organic compounds, an organic solvent, an acid, and a base;
- and wherein the plurality of organic compounds, the acid and the base are present in an amount effective to stabilize the plurality of carbocations.
8 more elements
Dependencies are inferred from the claim text.