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Fluorination in Medicinal Chemistry
BYRonald Mensah
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Introduction Fluorination methods Fluorination in Medical chemistry Conclusion Writing Component References Questions
Outline
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Introduction
What is fluorine? Location on the
periodic table Electronegativity Ionization energy Natural abundance
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=24065. accessed on 10/2/2014
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Electrophilic Fluorinations
Nucleophilic Fluorinations
Procedures
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What occurs in electrophilic fluorination reaction?
Cationic fluorine atom N-F and 0-F reagent Removal of electron density
Electrophilic Fluorination
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Electrophilic addition
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Direct displacement with fluoride
Protic vs aprotic solvent tetrabutylammoniumfluoride(TBAF)
Other Regents HF (diethylamino)-sulfur trifluoride (DAST)
Use of transition metals
Nucleophilic fluorination.
http://www.sigmaaldrich.com/catalog/product/aldrich/216143?lang=en®ion=US
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Nucleophilic Fluorination mechanism
H---F
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Orthogonal reactivity of Hydrogen and
Fluoride H+ vs F+
H- vs F-
enzyme activity design 5-fluorouracil (5-FU) pyridoxal phosphate (PLP)-dependent enzyme-
catalyzed reactions
Medicinal Chemistry
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5-fluorouracil (5-FU)
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DFMO (Eflornithine)
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Conclusion
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References
Banks, Alton. "Fluorine." Journal of Chemical Education 67.5 (1990): 373. ACS. Web
Kirk, Kenneth L. "Fluorination in Medicinal Chemistry: Methods, Strategies, and Recent Developments." Organic Process Research & Development 12.2 (2008): 305-21.
Lal, G. Sankar, Guido P. Pez, and Robert G. Syvret. "Electrophilic NF Fluorinating Agents." Chemical Reviews 96.5 (1996): 1737-756. Print.
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Questions?