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US 10,590,057 B2Granted
Isotopic fluorination and applications thereof
AssigneeThe Trustees of Princeton University
InventorsJohn T. Groves, Xinyi Chen
Life of this patent
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Abstract
Methods of C—H bond fluorination using non-heme manganese catalyst are described herein. For example, a method comprises providing a reaction mixture including a non-heme manganese catalyst, a substrate comprising an sp3 C—H bond and a fluorinating agent and converting the sp3 C—H bond to a C—F bond in the presence of the non-heme manganese catalyst or a derivative thereof.
Claims25
A method of fluorination comprising:
- providing a reaction mixture including a non-heme manganese catalyst, a substrate comprising an sp3 C—H bond and a fluorinating agent;
- and
- converting the sp3 C—H bond to a sp3 C—F bond via transfer of fluorine to the substrate from a cis-F—Mn—OH species of the non-heme manganese catalyst, wherein the non-heme manganese catalyst is selected from the group consisting of Mn(mep)F2, Mn(mcp)(OTf)2, Mn(mcp)(OH)(F), Mn(mcp)(O)(F), Mn(pdp)(OTf)2, Mn(pdp)(OH)(F), and Mn(pdp)(O)(F).
A method of fluorination comprising:
- providing a reaction mixture including a non-heme manganese catalyst, a substrate comprising an sp3 C—H bond and a fluorinating agent;
- and
- converting the sp3 C—H bond to a sp3 C—F bond via transfer of fluorine to the substrate from an equatorial ligand position on the non-heme manganese catalyst, wherein the reaction mixture is free of phase transfer catalyst, and the non-heme manganese catalyst is selected from the group consisting of Mn(mep)F2, Mn(mcp)(OTf)2, Mn(mcp)(OH)(F), Mn(mcp)(O)(F), Mn(pdp)(OTf)2, Mn(pdp)(OH)(F), and Mn(pdp)(O)(F).
Dependencies are inferred from the claim text.