Selective fluorination of organic compounds continues to be a
stimulating and exciting area of research. While a variety of fluorinating
reagents and methodologies have been developed to fulfill the increasing
demand for site selective fluorination of organic compounds, applications
of Deoxofluor and DAST continue to be used widely. Our interest
in applying synthetic methods for introducing fluorine or a fluorinated
group into a large variety of organic compounds encouraged this
review which highlights recent progress in fluorination reactions
using Deoxofluor [bis(2-methoxyethyl)aminosulfur trifluoride] and
DAST (diethylaminosulfur trifluoride) as key nucleophilic fluorinating
reagents. This review covers the literature for fluorination reactions
of organic compounds using Deoxofluor and DAST from January 1999
through July 2002.
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1 Introduction
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2 Synthesis of Deoxofluor [Bis(2-methoxyethyl)aminosulfur
Trifluoride] and DAST (Diethylaminosulfur Trifluoride)
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3 Fluorination Reactions with Deoxofluor and DAST
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3.1 Alcohols, Amino Alcohols, and Diols
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3.2 Carbohydrates
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3.3 Aldehydes and Ketones
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3.4 Dicarbonyls
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3.5 Sulfides, Sulfoxides, Thioesters and Thiocarbonyls
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3.6 Carboxylic Acids and Acid Chlorides
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3.7 Glyoxal Hydrates and Anhydrous Glyoxals
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3.8 Epoxides (Oxiranes)
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3.9 Peptides
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3.10 Ketoximes
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4 Miscellaneous Reactions
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4.1 Synthesis of Functionalized Oxazolines and Oxazoles
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4.2 Synthesis of Amides from Carboxylic Acids
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4.3 Synthesis of Cholest-5-ene-3β,4β-diyl
Diacetate (Steroid)
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4.4 Cycloetherization
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5 Reaction Mechanisms Using Deoxofluor and DAST
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5.1 Alcohols
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5.2 Aldehydes and Ketones
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5.3 Carboxylic Acids
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5.4 Sulfoxides
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5.5 Glyoxal Hydrates
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5.6 Ketoximes
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6 Conclusions
Deoxofluor - DAST - nucleophilic reactions - fluorination - halogenation
