Late-Stage Fluorination

Late-Stage Fluorination

Ritter, Tobias

Abstract:

The unnatural isotope fluorine–18 (18F) is used as a positron emitter in molecular imaging. Currently, many potentially useful 18F-labeled probe molecules are inaccessible for imaging, because no fluorination chemistry is available to make them. Syntheses must be rapid on account of the 110-minute half-life of 18F and benefit from using [18F]fluoride due to practical access and suitable isotope enrichment. But [18F]fluoride chemistry has been limited to nucleophilic fluorination reactions. I will describe the development of a palladium-based electrophilic fluorination reagent derived from fluoride and its application to the synthesis of aromatic 18F-labeled molecules via late-stage fluorination. In addition, I will discuss new reaction chemistry for introduction of fluorine into functionalized molecules. Late-stage fluorination enables the synthesis of conventionally unavailable positron emission tomography (PET) tracers for anticipated applications in pharmaceutical development as well as pre-clinical and clinical PET imaging.

The unnatural isotope fluorine–18 (18F) is used as a positron emitter in molecular imaging. Currently, many potentially useful 18F-labeled probe molecules are inaccessible for imaging, because no fluorination chemistry is available to make them. Syntheses must be rapid on account of the 110-minute half-life of 18F and benefit from using [18F]fluoride due to practical access and suitable isotope enrichment. But [18F]fluoride chemistry has been limited to nucleophilic fluorination reactions. I will describe the development of a palladium-based electrophilic fluorination reagent derived from fluoride and its application to the synthesis of aromatic 18F-labeled molecules via late-stage fluorination. In addition, I will discuss new reaction chemistry for introduction of fluorine into functionalized molecules. Late-stage fluorination enables the synthesis of conventionally unavailable positron emission tomography (PET) tracers for anticipated applications in pharmaceutical development as well as pre-clinical and clinical PET imaging.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-8-ritter_15th_BMOS

Referências bibliográficas

• [1] 1 E. Lee, A. S. Kamlet, D. C. Powers, C. N. Neumann, G. B. Boursalian, T.
• [2] Furuya, D. C. Choi, J. M. Hooker, T. Ritter Science 2011, 334, 639–642.
• [3] 2 E. Lee, J. M. Hooker, T. Ritter J. Am. Chem. Soc. 2012, 134, 17456–
• [4] 17458.

Como citar:

Ritter, Tobias; "Late-Stage Fluorination", p-323-323. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-8-ritter_15th_BMOS