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Monofluorinated Heterocycles

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Halogenated Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 27))

Abstract

The chapter presents an overview of synthetic chemistry of ring-fluorinated heterocycles containing only one fluorine atom (monofluorinated heterocycles). Particular attention is given to modern nucleophilic and electrophilic fluorination methods, including catalytic reactions, chiral and microwave-assisted synthesis, carbene and hypervalent chemistry, utilization of ionic intermediates and ionic liquids, and others. One of the major emphases of the chapter is identification of the remaining “white spots” as opportunities for the future research effort.

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Abbreviations

Accufluor®:

1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis-tetrafluoroborate

CEFOX:

Cesium fluoroxysulphate

DAST:

Diethylaminosulfur trifluoride

Deoxo-Fluor®:

Bis(2-methoxyethyl)aminosulfur trifluoride

EMEF:

N-Ethyl(hexamethylenetetraammonium) fluoride

NBS/Et3N•3HF:

N-Bromsuccinimide/Et3N•3HF

NFSI:

N-Fluorobenzenesulfonimide

“Proton sponge”/Et3N•3HF:

1,8-Bis(dimethylamino)naphthalene/Et3N•3HF

Selectfluor®:

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-tetrafluoroborate

TBAF (Bu4NF):

Tetrabutylammonium fluoride

TMAF (Me4NF):

Tetramethylammonium fluoride

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Acknowledgments

This chapter – a contribution from the Discovery Chemistry Project – is dedicated to the memory of Kirill Gennadievich Nikishin (1967–2010).

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  1. National Institutes of Health, NIDDK, 8 Center Drive, Bethesda, MD, 20892, USA

    Andrei A. Gakh

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  1. Andrei A. Gakh
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Correspondence to Andrei A. Gakh .

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  1. , Department of Physical and Organic Chemi, "Jozef Stefan" Institute, Jamova 39, Ljubljana, 1000, Slovenia

    Jernej Iskra

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Gakh, A.A. (2011). Monofluorinated Heterocycles. In: Iskra, J. (eds) Halogenated Heterocycles. Topics in Heterocyclic Chemistry, vol 27. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_58

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