18F-Difluoromethyl(ene) Motifs via Oxidative Fluorodecarboxylation with 18FFluoride

18F-Difluoromethyl(ene) Motifs via Oxidative Fluorodecarboxylation with 18FFluoride

Herein, we report that α-fluorocarboxylic acids undergo manganese-mediated oxidative 18F-fluorodecarboxylation with [18F]fluoride affording biologically relevant 18F-difluoromethyl(ene)-containing molecules. This no-carrier added process provides a solution to a known challenge in radiochemistry and...

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Veröffentlicht in:Organic letters 2024-11, Vol.26 (43), p.9368
Hauptverfasser: Ortalli, Sebastiano, d, Joseph, Szpera, Robert, Stoessel, Barbara, Trabanco, Andrés A, Tredwell, Matthew, Gouverneur, Véronique
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container_end_page
container_issue 43
container_start_page 9368
container_title Organic letters
container_volume 26
creator Ortalli, Sebastiano
d, Joseph
Szpera, Robert
Stoessel, Barbara
Trabanco, Andrés A
Tredwell, Matthew
Gouverneur, Véronique
description Herein, we report that α-fluorocarboxylic acids undergo manganese-mediated oxidative 18F-fluorodecarboxylation with [18F]fluoride affording biologically relevant 18F-difluoromethyl(ene)-containing molecules. This no-carrier added process provides a solution to a known challenge in radiochemistry and expands the radiochemical space available for positron emission tomography (PET) ligand discovery. Scalability on a fully automated radiosynthetic platform is exemplified with the production of [18F]4,4-difluoropiperidine that, we demonstrate, is amenable to postlabeling functionalization including N-heteroarylation and amide as well as sulfonamide bond formation.Herein, we report that α-fluorocarboxylic acids undergo manganese-mediated oxidative 18F-fluorodecarboxylation with [18F]fluoride affording biologically relevant 18F-difluoromethyl(ene)-containing molecules. This no-carrier added process provides a solution to a known challenge in radiochemistry and expands the radiochemical space available for positron emission tomography (PET) ligand discovery. Scalability on a fully automated radiosynthetic platform is exemplified with the production of [18F]4,4-difluoropiperidine that, we demonstrate, is amenable to postlabeling functionalization including N-heteroarylation and amide as well as sulfonamide bond formation.
doi_str_mv 10.1021/acs.orglett.4c03611
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title 18F-Difluoromethyl(ene) Motifs via Oxidative Fluorodecarboxylation with 18FFluoride
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